Pyrimidine, 4-amino-5-benzoyl

Cyclization of methyl 2-[2-benzoyl-2-ethoxycarbonyl-l-vinyl)amino]-3-[(4-methyl-2-pyridyl)amino]acrylate (311) afforded the 3-amino-8-methyl-4//-pyrido[l,2-n]pyrimidin-4-one derivative 312 (97JHC1511). 

Hydroxy-L-prolin is converted into a 2-methoxypyrrolidine. This can be used as a valuable chiral building block to prepare optically active 2-substituted pyrrolidines (2-allyl, 2-cyano, 2-phosphono) with different nucleophiles and employing TiQ as Lewis acid (Eq. 21) [286]. Using these latent A -acylimmonium cations (Eq. 22) [287] (Table 9, No. 31), 2-(pyrimidin-l-yl)-2-amino acids [288], and 5-fluorouracil derivatives [289] have been prepared. For the synthesis of p-lactams a 4-acetoxyazetidinone, prepared by non-Kolbe electrolysis of the corresponding 4-carboxy derivative (Eq. 23) [290], proved to be a valuable intermediate. 0-Benzoylated a-hydroxyacetic acids are decarboxylated in methanol to mixed acylals [291]. By reaction of the intermediate cation, with the carboxylic acid used as precursor, esters are obtained in acetonitrile (Eq. 24) [292] and surprisingly also in methanol as solvent (Table 9, No. 32). Hydroxy compounds are formed by decarboxylation in water or in dimethyl sulfoxide (Table 9, Nos. 34, 35). 

Mendel44 found that reaction of 2-aminopyridine-3-carboxylic acid with ethyl acetoacetate or ethyl benzoylacetate gave rise to a decarboxylated product (36 R1 = Me, Ph R = R2 = H), whereas with ethyl 4,4,4-tri-fluoroacetoacetate, the product was ethyl 2-aminopyridine-3-carboxylate. Yale51 obtained 3-benzoyl-2-hydroxy-4-oxo-4ff-pyrido[ 1,2-a] pyrimidine in 4- 5%, yield from 2-amino-3-methylpyridine and ethyl benzoylacetate in diethylbenzene. 

Cytidine and related pyrimidine nucleosides have also been synthesized by the mercuri procedure.198 In the case of the cytosine nucleoside, prior blocking of the amino function is necessary, in order to obtain a mercury derivative [(-V-acetylcytosine)mercury] adaptable for nucleoside synthesis. Reaction of one mole of LV with two moles199 of tri-O-benzoyl-D-ribofuran-... 

This synthesis involves Michael cycloaddition reaction of the readily available 4-hydroxycoumarine 1 with a cyanocrotonitrile 2 in ethanolic piperidine to afforded 2-amino-3-cyano-4-methyl-4H, 5H-pyrano-benzopyran-5-one (3). Treatment of 3 with acetic anhydride for 0.5 h and/or 3 h under reflux afforded N-acetyl and [l]benzopyrano[3/,4/ 5,6]pyrano(2,3-d) pyrimidine-6,8-dione derivatives (4) and (5a), respectively. Also, interaction of 3 with benzoyl chloride or formic acid gave the corresponding pyrimidine derivatives (5b,c) while its treatment with formamide afforded the aminopyrimi-dine derivative (6). 

Preparation of ( )- 3-[[l-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo-[5,4-d]pyrimidin-6-yl)-propyl]-(4-methyl-benzoyl)-amino]-propyl -carbamic acid t-butyl ester... 

Attempts to use basic reaction components other than 2,4-dialkoxy-pyrimidines met with varied success. Thus, the early attempt of Hilbert30 to react a-acetobromoglucose with 4-amino-2-methoxy-pyrimidine (19) failed. On the other hand, when 4-ethoxy-2(lI/)-pyrimidinone (20) or l-methyl-4-methoxy-2(li/)-pyrimidinone (21) was condensed with 2,3,5-tri-O-benzoyl-D-ribofuranosyl chloride, moderate yields were obtained of 3-/9-D-ribofuranosyluracil (22) and its 1-methyl derivative (23), respectively.31... 

Pyrimidine 6-Amino-5-benzoyl-2-bromo-4-cyan- E9b/2, 20 [Br-CN + Ar-CO-C(CN) = C(NH2)-CC13]... 

Pyrimidin 5-(2-Hydroxy-benzoyl)-2-methyl- E9b/2, 170f. (3-CHO 4H-chromon + Acetamidin) Quinazolin 2-(2-Furyl)-4-methyl- -3-oxid E9b/2, 18 [2-(NH-CO-Het) —Ar— 1-CR = N —OH/H+] Quinolin 3-Amino-4-hydroxy-2-oxo-1 -(2-propinyl)-l, 2-dihydro-E15/2, 1251 (1,3-Oxazol-Spalt.)... 

Condensation of 17 with thiourea gave the corresponding 4-imino-thieno[2,3-d]pyrimidine-2(l/7)-thiones 32 (92PS93 93PHA347). With PhCONCS, however, the 3-benzoyl-4-imino derivative 32 (R = COPh) (92PS93) or the 4-amino derivatives 33 (R - H) [89AP227 91EGP-(D)287503] were obtained. 

The IR spectra of Co(II), Ni(II) and Cu(II) complexes of Schiff bases derived from condensation of 2-pyridine-carboxaldehyde with DL-alanine, DL-valine and DL-phenylalanine, show that all act as uninegative, bidentate ligands.507 Similar data for complexes of the heterocyclic Schiff base LH2 derived from 1 -amino-5-benzoyl-4-phenyl-li/-pyrimidin-2-one and 3-hydroxy-salicylalde-hyde show that the ligand is tridentate (0,N,0) in M(LH)2 (M = Co, Cu, Zn), but bidentate (N,0) in Ni(LH2)2Cl2.508... 

Besides formyl, other acyl groups such as acetyl or benzoyl in the 5-position of the pyrimidine nucleus have been used for cyclizations. Thus, 5-acyl-6-aminopyrimidin-4(3//)-ones condense with malononitrile in refluxing pyridine to give the corresponding 7-amino-4-oxo-3,4-dihydropyrido[2,3-(7]pyrimidine-6-carbonitriles 21.171... 

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