101375-08-0

Basic information

• Product Name: N-<4-<<(2,4-diamino-5-methylpyrido<2,3-d>pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamic acid diethyl ester
• Synonyms: N-<4-<<(2,4-diamino-5-methylpyrido<2,3-d>pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamic acid diethyl ester
• CAS NO: 101375-08-0
• Molecular Weight: 509.565
• Mol File: 101375-08-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-<4-<<(2,4-diamino-5-methylpyrido<2,3-d>pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamic acid diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-<4-<<(2,4-diamino-5-methylpyrido<2,3-d>pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamic acid diethyl ester(101375-08-0)
• EPA Substance Registry System: N-<4-<<(2,4-diamino-5-methylpyrido<2,3-d>pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamic acid diethyl ester(101375-08-0)

Safety Data

• Hazardous Substances Data: 101375-08-0(Hazardous Substances Data)

Upstream product

• 101348-14-5 3-cyano-5-<(methoxymethoxy)methyl>-4-methyl-2-(methylthio)pyridine 
• 101348-12-3 3-cyano-5-(ethoxycarbonyl)-4-methylpyridine-2(1H)-thione 
• 101375-07-9 ethyl 3-cyano-4-methyl-2-(methylthio)nicotinate 
• 101348-13-4 3-cyano-5-(hydroxymethyl)-4-methyl-2-(methylthio)pyridine 
• 101810-71-3 2-amino-4-methyl-3,5-pyridinedicarbonitrile 
• 101348-31-6 2,4-diamino-6-(hydroxymethyl)-5-methylpyrido<2,3-d>pyrimidine 
• 101348-30-5 6-(acetoxymethyl)-5-methylpyrido<2,3-d>pyrimidine-2,4(1H,3H)-dione 
• 64829-09-0 2-amino-6-chloro-4-methyl-3,5-pyridinedicarbonitrile 
• 13726-52-8 diethyl N-(p-aminobenzoyl)-L-glutamate 
• 101810-73-5 2,4-diamino-5-methylpyrido<2,3-d>pyrimidine-6-carbonitrile 
• 101348-32-7 2,4-diamino-6-(bromomethyl)-5-methylpyrido<2,3-d>pyrimidine 
• 5900-40-3 2,4-dioxo-6-methyl-1,2,3,4-tetrahydro-5-pyrimidinecarbonitrile 
• 3788-94-1 2-ethoxymethylene-3-oxobutanoic acid ethyl ester 
• 101348-27-0 C₁₅H₁₉N₅O₆ 

Downstream Products

• 101348-00-9 N-pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamic acid 
• 101810-81-5 5,10-dimethyl-5-deazafolic acid 
• 101810-79-1 5-methyl-5-deazamethotrexate 
• 101348-20-3 N-pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamic acid 

Relevant articles and documents

Synthesis and Biological Activities of 5-Deaza Analogues of Aminopterin and Folic Acid

N-pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamic acid (1a, 5-deazaaminopterin) and the 5-methyl analogue (1b) were synthesized in 14 steps from 5-cyanouracil (4a) and 5-cyano-6-methyluracil (4b), respectively, by exploitation of the novel pyrimidine to pyridopyrimidine ring transformation reaction.The 5-cyanouracils 4 were treated with chloromethyl methyl ether to the 1,3-bis(methoxymethyl)uracils (5, which were treated with malononitrile in NaOEt/EtOH to give the pyridopyrimidines 6.Diazotization of 6 in concentrated HCl afforded the 7-chloro derivatives 8 in high yield.After reduction of 8, the 7-unsubstituted products 9 were reduced in the presence of Ac2O and the products, 6-(acetamidomethyl)pyridopyrimidines 10, were converted into the 6-acetoxymethyl derivatives 12 via nitrosation.After removal of the N-methoxymethyl groups from 12, the 6-(acetoxymethyl)pyridopyrimidine 2,4(1H,3H)-diones 14 were converted into 2,4-diamino-6-(hydroxymethyl)pyridopyrimidine (15a) and its 5-methyl analogue 15b by the silylation-amination procedure.Compounds 15 were brominated to the 6-bromomethyl derivatives 16, which were treated with diethyl (p-aminobenzoyl)-L-glutamate, and the products 17 were saponified to afford 5-deazaaminopterin (1a) and its 5-methyl analogue 1b.Compopund 1b was also prepared by an alternative procedure in 10 steps from cyanothioacetamide and ethyl β-(ethoxymethylene)acetoacetate via 2,4-diamino-6-(hydroxymethyl)-5-methylpyridopyrimidine (15b). 5-Deaza-5-methylfolic acid (2) was also prepared in four steps from 15b.The aminopterine analogues 1 showed significant anticancer activity in vitro and in vivo, whereas thefolic acid analogue 2 did not exhibit any significant toxicity.