Methyl pyrimidine-4-carboxylate → 4-Pyrimidinecarboxylic acid

HRID 1671469

Reaction equation

HRID 1671469 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][N:6]=1)=[O:4].BrC1C(C(O)=S)=NC(C)=NC=1>[Ni]>[N:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 254248Methyl pyrimidine-4-carboxylateHCID 178432654HCID 178432654, compound

Product 1

HCID 1693064-Pyrimidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

While J. Org. Chem., 30, 2398 (1965) describes that methylpyrimidine-4-carboxylate can be synthesized by treating 5-bromo-2-methylthiopyrimidine-4-carboxylic acid with Raney-nickel, as described in J. Chem. Soc., 1953, 3129, to give pyrimidine-4-carboxylic acid, and heating the obtained compound in methanol in the presence of concentrated hydrochloric acid. This method is problematic in the availability of the starting materials.

Workup

  1. customcan be synthesized

Sources & evidence

ORD record
ord-d5a16c132df441b6816d964009780896
Source dataset
uspto-grants-2011_08
Patent number
US07994315B2

Linked notes

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