4.5- Diamino-2-methylamino

Chemical Name N-(4-([(2,4-Diamino-6-pteridinyl)methyl] methylamino] -benzoyl] -L-glutamic acid... 

Chemical Name 0-2,6-diamino-2,3,4,6-tetradeoxy-0 -D-glvcero-hex-4-enopvranosvl-(1 > 4)-0-[3-deoxv-4-C-methvl-3-(methylamino)- 3-L-arabinopvranosvl-(1 6)] -2-deoxy-D-strept-amine... 

Such names as bacillosamine for 2,4-diamino-2,4,6-trideoxy-D-glucose and garosamine for 3-deoxy-4-C-methyl-3-methylamino-L-arabinose are not recommended, as they imply replacement of OH by NH2 in a nonexistent parent sugar. 

CN 4-amino-1 -[(aminoacetyl)methylamino]-1,4-dideoxy-3-0-(2,6-diamino-2,3,4,6,7-pentadeoxy-p-L-Zyj o-... 

CN 0-3-deoxy-4-C-methyl-3-(methylamino)-p-L-arabinopyrasoyl-(l->6)-0-[2,6-diamino-2,3,4,6-tetradeoxy-a-D-g/ycera-hex-4-enopyranosyl-(l->4)]-2-deoxy-D-streptamine... 

By contrast, alkylamination of naphthazarin (7) in the presence of sodium dithionite followed by oxidation gives l,4-bis(alkylamino)-5,8-naphthoquinone (31).18,19 However, Kikuchi and co-workers20 obtained isomeric l,5-bis(alkylamino)-4,8-naphthoquinone (32) from the reaction of leuco naphthazarin (33) with alkylamine They also isolated 5-alkylamino-leuco-naphthazarin (34) as an intermediate, which is further aminated at the 1-position to give 32. Bloom and Dudek21 have studied the structure of leuco aminonaphthoquinones and their tautomeric equilibria in solution. They concluded that the reaction of leuco naphthazarin (33) or the leuco compound (35) derived from l,5-diamino-4,8-naphthoquinone (36) with methylamine gives mixtures of l,4-bis(methylamino)-31 (R = Me) and 1,5-bis(methylamino)naphthoquinones 32 (R = Me) after oxidation of leuco aminonaphthoquinones (Scheme 10). Some of the structures of leuco aminonaphthoquinones are shown in Scheme ll.20... 

C15H3i5N405 3.5 H20 0-(2,6-Diamino-2,3,4,6-tetradeoxy-6-C-methyI-a - d - en/thro-hexopyranosyl) - (1 — 4) - l - 3 - amino -1,3,6- trideoxy -1 -methoxy-6-(methylamino)-chiro-inositol, hydrate (fortimicin B, hydrate) (FORTBH)52... 

Diamino-6-[(2,4,6-trimethylphenyl)methylamino]pyridine was reacted with EMME in boiling dioxane for 30 min to give 3-pyridylamino-methylenemalonate (169) in 73% yield (79CZ387). 

The nitration of 1,1,2,2-tetraiodoethylene (182) with 90% nitric acid provides 1,1-diiododinitroethylene (183) in good yield. Baum and co-workers studied the chemistry of 1,1-diiododinitroethylene and found that displacement of the two vinylic iodide groups is effected by treatment with simple aliphatic amines, diamines and anilines to give 1,1-diamino-2,2-dinitroethylenes in excellent yield. Cyclic products are obtained from the reaction of 1,1-diiododinitroethylene with 1,2-diaminoethane (ethylenediamine), 1,3-diaminopropane and 1,4-diaminobutane. The spirocycle (184) is synthesized from the reaction of 1,1-diiododinitroethylene (183) with 2,2-bis(methylamino)-l,3-diaminopropane. 

Methotrexate Methotrexate, N- p-[[2,4-diamino-6-piperidinyl)methyl]methylamino]-benzoyl]-L-( )-glutamic acid (30.1.1.8), is made by reacting A-(4-methylaminoben-zoyl)glutaminic acid (30.1.1.3) with 2-amino-4-hydroxyl-6-bromomethylpteridine... 

Die N-alkylierten, substituierten o-Diamino-arene sind oft instabil und nicht rein zu isolieren. Sie sind nichtsdestoweniger begehrt, weil sie regiospezifisch zu den entsprechenden N-Alkyl-benzimidazolen cyclisieren. Die katalytische Reduktion von 2-Nitro-Gruppen zu 2,6-Diamino-3-methylamino-benzonitril kann in einer Eintopf-Synthese mit der Orthoester-Cyclisierung kombiniert werden205. 

Methylamino-l,6-naphthyridine-3-carbonitrile (18, R = Me) underwent limited hydrolysis of its cyano group to afford 2-methylamino-l,6-naphthyridine-3-carboxamide (17) (KOH, H20, EtOH, reflux, 5 min 79%) the related substrate, 2-amino-l,6-naphthyridine-3-carbonitrile (18, R = H), underwent thiolysis of the cyano group to afford 2-amino-1,6-naphthyridine-3-car-bothioamide (19) (substrate, NEt3, pyridine, 20°C, H2S in, 2 h 97%) or hydrazinolysis of the cyano group to afford 2,N diamino -1,6-naphthyridine-3-carboxamidine (20) (H2NNH2.H2Q, reflux, 5 min 65%).247... 

By contrast, however, 3,5-diamino-l,2,4-thiadiazoles are selectively converted into amides and sulfonamides in good yields. Thus, acetylation of 3,5-diamino-l,2,4-thiadiazole (53) with excess acetic anhydride yields the symmetrical derivative (133) whereas under similar conditions 3-amino-5-methylamino-l,2,4-thiadiazole and 3,5-diarylamino-l,2,4-thiadiazoles (65AHC(5)119) produce the monoacylated derivatives (134) and (135), respectively. Sulfonylation also results in the preferential formation of the 3-sulfonamides but reaction with excess reagent eventually produces the 3,5-disubstituted derivatives (136) and (137) in good yields (65AHC(5)119). 

Most such pyrazinones have been made by primary synthesis (Chapters 1 and 2) or N-alkylation of tautomeric pyrazinones (Section 5.1.2.2). The minor route by rearrangement of alkoxypyrazines (H 184) appears to be unpresented in recent literature, but there are examples of the hydrolysis of nontautomeric iminopyrazines to corresponding pyrazinones. Thus 3-imino-4-methyl-3, 4-dihy-dro-2-pyrazinamine hydriodide (191, R = H) (i.e., 2,3-diamino-l-methyl-pyrazinium iodide) underwent hydrolysis in 2 M sodium hydroxide during 1 h at 100°C to afford 3-amino-1 -methyl-2(l//)-pyrazinonc (192, R = H) ( 40%) without any evidence of Dimroth rearrangement to 3-methylamino-2-pyrazinamine 1008 l-methyl-3-methylamino-2(l//)-pyrazinimine (191, R = Me) likewise gave 1-methyl-3-methylamino-2(l//)-pyrazinone (192, R = Me) ( 50%) 1008 and other examples have been reported.598... 

Methyl 6-chloro-2-pyrazinecarboxylate Methyl 5-chloro-2-pyrazinecarboxylate 1-oxide Methyl 6-chloro-2-pyrazinecarboxylate 4-oxide Methyl 6-chloro-3-thioxo-3,4-dihydro-2-pyrazinecarboxylate Methyl 3-cyano-5,6-diphenyl-2-pyrazinecarboximidate Methyl 3-cyano-2-pyrazinecarboxylate Methyl 5-cyano-2-pyrazinecarboxylate Methyl 3- (IV-cyclopropyl-lV-methylamino)-2-pyrazinecarboxylate Methyl 3,5-diamino-6-benzoyl-2-pyrazinecarboxylate Methyl 3,5-diamino-6-bromo-2-pyrazinecarboxylate Methyl 3,5-diamino-6-chloro-2-pyrazinecarboxylate Methyl 3,5-diamino-6-(l-hydroxyethyl)-2-pyrazinecarboxylate Methyl 3,5-diamino-6-iodo-2-pyrazinecarboxylate Methyl 3,5-diamino-2-pyrazinecarboxylate Methyl 3,6-dibromo-2-pyrazinecarboxylate... 

Addition of cyclohexyl isocyanide to 4-amino-l-chroma-l,3-dienes ( )-96b-e provides a mild and regiospecific access to l,4-diamino-2-ethoxy naphthalenes 104 [l-NHc-QHn 4-NRR1 = NMe2, (S)-2-hydroxymethyl-pyrrolidinyl, (lf ,25)-2-methylamino-l-phenyl-l-propanol, N-f-BuMe] in... 

Escherichia coli B was incubated with 2,6-diaminopurine (XXIV), and 6-amino-2-(methylamino)-9-(5-0-phospho-D-ribosyl)purine (XXV) was isolated from the acid-soluble extract of the cells. 5-Nucleotidase liberated a nucleoside containing D-ribose. Hydrolysis of the nucleoside (or nucleotide) with N hydrochloric acid liberated 6-amino-2-(methylamino)purine, which was identified by paper chromatography and by its ultraviolet absorption spectrum. The chromatographic and ion-exchange behavior of the extract also suggested the presence of either a pyrophosphate or a triphosphate of the 6-amino-2-methylamino-(D-ribosyl)purine. In a similar manner, 2,6-diamino-9-(5-0-phospho-D-ribosyl)purine (XXVI) was isolated and identified, together with its possible pyrophosphate or triphosphate. 2,6-... 

The synthesis of 6-amino-2-methylamino-purine from 2,6-diamino-purine and the corresponding nucleotides was also demonstrated in crude extracts of Escherichia coli B. 

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