Pyrimidines diamino

Other names 2,4-Diamino-5-(3,4,5-trimethoxybenzyl) Pyrimidine, 2,4-Diamino-5-(3,4,5 -trimethoxybenzyl) pyrimidine)... 

Many patents have been issued on the use of pyrogaUol derivatives as pharmaceuticals. PyrogaUol has been used extemaUy in the form of an ointment or a solution in the treatment of skin diseases, eg, psoriasis, ringworm, and lupus erythematosus. GaUamine triethiodide (16) is an important muscle relaxant in surgery it also is used in convulsive-shock therapy. Trimethoprim (2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine) is an antimicrobial and is a component of Bactrin and Septra. Trimetazidine (l(2,3,4-trimethoxybenzyl)piperazine (Vastarel, Yosimilon) is used as a coronary vasodilator. l,2,3,4-Tetrahydro-6-methoxy-l-(3,4,5-trimethoxyphenyl)-9JT-pyrido[3,4- ]indole hydrochloride is useful as a tranquilizer (52) (see Hypnotics, sedatives, ANTICONVULSANTS, AND ANXIOLYTICS). Substituted indanones made from pyrogaUol trimethyl ether depress the central nervous system (CNS) (53). Tyrosine-and glycine(2,3,4-trihydroxybenzyl)hydrazides are characterized by antidepressant and anti-Parkinson activity (54). 

Pyrimidine-2-thione, 4,5-diamino-S-alkylation, 3, 94 Pyrimidine-2-thione, dihydrosynthesis, 3, 109... 

Pyrimido[5,4-d]pyrimidine, 6,8-diamino-4-hydroxy-2-phenyl-synthesis, 3, 364... 

For the preparation of triazolopyrimidines three main types of synthesis are in use. The first of these proceeds from a pyrimidine derivative (especially the 4,5-diamino derivatives) and closes the triazole ring. The second method proceeds, on the contrary, from derivatives of u-triazole to close the pyrimidine ring. The third method finally is one which yields the derivatives through substitution or replacement of substituents in compounds prepared by one of the first-named procedures. 

The catalytic effect of protons, of bifunctional catalysts, and of base is demonstrated in the amination of chloro derivatives of pyridazine, pyrimidine, and s-triazine (Tables V and VI). Anilino-s-triazines containing NH groups act as catalysts in their own formation. The catalytic action of protons on anhino-dechlorination of 2-chloro-4,6-diamino-s-triazine and of 2-amino-4-chloropyrimidine was reported in the classic paper by Banks. ... 

Attempted dehydrocyclization of the 6-acylhydrazinopyrimidine 65 by heating with polyphosphoric acid led, instead, to pyrimidine ring rupture, yielding the l,l-diamino-2-nitro-2-(3-phenyl-l,2,4-triazol-5-yl)ethene 66. Cyclocondensation of the latter with triethyl orthoformate gave the fully aromatic triazolopyrimidine 67 (94JHC1171) (Scheme 23). 

Treatment of 5,7-diamino-l,3,4-thiadiazolo[3,2-n]pyrimidinium ehloride (25) with Vilsmeier reagent gave the 7-formamido-l,2,4-triazolo[l,5-c]pyrimidin-5-one (27) (90JHC851) (Seheme 42). Compound 27 has presumably been formed via rupture of the 1,3,4-thiadiazole ring of 25 and... 

Fluorophenylacetyl and 4-fluorophenylacetyl chlorides selectively ac-ylated the C8-NH2 group of 7,8-diamino-l,2,4-triazolo[l,5-c]pyrimidine 139 (94JHC1171) to give 140 (Scheme 54) N6 of the ring system probably renders the closer C7-NH2 group less nucleophilic than the remoter C8-NH2 function. 

The 3-amino group of 3,4-diamino-2//-pyrido[l,2-u]pyrimidin-2-ones 216, obtained from 3-nitroso derivatives by reduction with Na2S204 in 30% NH4OH at 70-80 °C, was acylated with acyl chlorides, and the acylated products 217 were cyclized to pyrido[2,l-Z)]purin-10-ones 218 by treatment with NaOMe (95JHC1725). 

A mixture of 2 g of 4,5-diamino-6-mercaptopyrimidine and 10 ml of 9B% formic acid was heated at 70°C for two hours and then evaporated to dryness on the steam bath to give as a residue, 7-amino-thiazolo (5,4-d) pyrimidine. 

It was known that the K+ -competitive imidazopyridine compound, SCH28080, inhibits acid secretion. Then, many reversible inhibitors were developed. These contain protonatable nitrogens but have a variety of core structures such as imidazopyiidines, piperidinopyr-idines, substituted 4-phenylaminoquinolines, pyrrolo [3,2-c]quinolines, guanidinothiazoles, and 2,4-diamino-pyrimidine derivatives. Several reversible inhibitors have been in clinical trials. 

Bei der Reduktion von Purinen wird zumeist der Funfring aufgespalten. Die galvano-statische Elektrolyse (3—4 A/8 V fur mehrere Stdn.) von 2,8-Diamino-purin in 25,8 n Schwefelsaure an Blei-Kathoden liefert neben 2,8-Diamino-1,2,3,4,5,6-hexahydro-9H-purin 2-Amino-5-guanidino-6-oxo-3,4,5,6-tetrahydro- und 2-Amino-5-guanidino-3,4-dihydro-pyrimidin (nur das Tetrahydro-pyrimidin-Derivat ist abtrennbar (Totalausbeute -45% d.Th.)3. 

---