2,6-Diaminopyrimidine-4-carboxylic acid → Methyl 2,6-diamino-4-pyrimidinecarboxylate

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([NH2:11])[N:3]=1.Cl.[CH3:13]O>>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:13])=[O:9])[CH:5]=[C:4]([NH2:11])[N:3]=1

Participants

Reactant 2

HCID 2405312,6-Diaminopyrimidine-4-carboxylic acid

HCID 21893726Hydrochloride methanol

Product 1

HCID 22476528Methyl 2,6-diamino-4-pyrimidinecarboxylateYield 100%

Procedure

2,6-diamino pyrimidine-4-carboxylic acid (G. D. Davies, F. Baiocchi, R. K. Robins and C. C. Cheng, J. Org Chem 26 (1961) 2755-2759) was esterified with HCl/MeOH using the procedure of Preparation 4, step (a) in 100% yield. 1HNMR δ(DMSO) 3.90(3H,s), 6.72 (1H,s), 8.57 (broad), 8.93 (broad).

Workup

customthe procedure of Preparation 4, step (a) in 100% yield

Sources & evidence

ORD record: ord-ffe772257b6c4f15b4a3ea6b943eee26
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972297B2

Reaction notes

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