80360-12-9

Basic information

• Product Name: N-(4-{[(2-amino-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidin-6-yl)methyl](methyl)amino}benzoyl)glutamic acid
• CAS NO: 80360-12-9
• Molecular Formula: C₂₁H₂₂N₆O₆
• Molecular Weight: 454.436
• Mol File: 80360-12-9.mol
• Article Data: 3

Chemical Properties

• Density: 1.54g/cm³
• Refractive Index: 1.708
• CAS DataBase Reference: N-(4-{[(2-amino-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidin-6-yl)methyl](methyl)amino}benzoyl)glutamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-{[(2-amino-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidin-6-yl)methyl](methyl)amino}benzoyl)glutamic acid(80360-12-9)
• EPA Substance Registry System: N-(4-{[(2-amino-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidin-6-yl)methyl](methyl)amino}benzoyl)glutamic acid(80360-12-9)

Safety Data

• Hazardous Substances Data: 80360-12-9(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 85597-17-7 5-deazafolic acid 
• 80360-10-7 N-[4-[[(2,4-Diaminopyrido[2,3-d]pyrimidine-6-yl)methyl]methylamino]benzoyl]-L-glutamic acid 
• 13726-52-8 diethyl N-(p-aminobenzoyl)-L-glutamate 
• 80360-04-9 2,4-Diamino-6-(carboxaldehyde)pyrido[2,3-d]pyrimidine 
• 80360-09-4 N-<4-<<(2,4-diaminopyrido<2,3-d>pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamic acid 
• 80360-11-8 diethyl 5-deazafolate 
• 80360-08-3 N-<4-<<(2,4-diaminopyrido<2,3-d>pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamic acid diethyl ester 
• 80360-03-8 2-amino-4(3H)-oxopyrido<2,3-d>pyrimidine-6-carboxaldehyde 

Relevant articles and documents

2,4-Diamino-6-(hydroxymethyl)pyrido[2,3-d]pyrimidine

There is disclosed a novel intermediate useful in the preparation of pyrido [2,3-d] pyrimidines, which includes N-[4-[(2-amino-4(3H)-oxopyrido[2,3-d]pyrimidin-6-yl)methylamino]benzoyl]-L-glutamic acid (5-deazafolic acid), N-[4-[[2-amino-4(3H)-oxopyrido[2,3-d]-pyrimidin-6-yl)methyl]methylamino]benzoyl]-L-glutamic acid (5-deaza-N10 -methylfolic acid), N-(4-[(2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)methylamino]benzoyl]-L-glutamic acid (5-deazaaminopterin), and N-[4-[[2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)methyl]methylamino]benzoyl]-L-glutamic acid (5-deazamethotrexate). This intermediate is the compound 2,4-diamino-6-(hydroxymethyl)pyrido-[2,3-d]pyrimidine.

Pyridopyrimidines. Synthesis of the 5-Deaza Analogues of Aminopterin, Methotrexate, Folic Acid, and N10-Methylfolic Acid

Reaction of bromoacetic acid with N,N-dimethylformamide and phosphorus oxychloride gave a triformylmethane derivative, which was condensed with 2,4-diaminopyrimidin-6(1H)-one (2) in water at reflux to give 2-amino-4(3H)-oxopyridopyrimidine-6-carboxaldehyde (4).The structure of 4 was confirmed by conversion to the 2,4-dinitrophenylhydrazone and oxidation to the known 6-carboxylic acid (6).Similarly, condensation of 1 with 2,4,6-triaminopyrimidine gave 2,4-diaminopyridopyrimidine-6-carboxaldehyde (5).Reductive alkylation of diethyl (p-aminobenzoyl)-L-glutamate (9) with 5 in 70percent acetic acid over Raney nickel gave diethyl N-pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamate (10), which was saponified with base to give the corresponding glutamic acid 11 (5-deazaaminopterin).The latter was methylated with formaldehyde and sodium cyanoborohydride to give 5-deazamethotrexate (12).Reductive alkylation of 9 with 4 gave diethyl N-pyrimidin-6-yl>methyl>amino>benzoyl>-L-glutamate (13), which was converted to the corresponding glutamic acid 14 (5-deazafolic acid).The preferred route for the preparation of 14 involved the hydrolysis of 10 with base at reflux, which resulted in replacement of the 4-amino group and saponification of the ester groups.Methylation of 14 with formaldehyde and sodium cyanoborohydride gave 5-deaza-10-methylfolic acid (15), which was also prepared by alkaline hydrolysis of the 4-amino group of 12.