Methanol → 2-(3-Methoxyphenyl)pyrimidine-5-carboxylic acid

HRID 2381965Notes

Reaction equation

HRID 2381965 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[N:9][CH:10]=1)=[O:4].O.[OH-].[Li+].CO.O>C1COCC1>[CH3:18][O:17][C:13]1[CH:12]=[C:11]([C:8]2[N:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][N:7]=2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 685580872-(3-Methoxy-phenyl)-pyrimidine-5-carboxylic acid methyl ester

Product 1

HCID 532117402-(3-Methoxyphenyl)pyrimidine-5-carboxylic acidYield 103.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(3-methoxy-phenyl)-pyrimidine-5-carboxylic acid methyl ester (145 mg, 0.59 mmol), lithium hydroxide monohydrate (49.5 mg, 1.18 mmol), MeOH (1.5 mL), water (1.5 mL) and THF (1.5 ml) is stirred at rt for 3.5 hrs. The reaction mixture is concentrated, and water (1 mL) and 1 N aqueous HCl (1.2 mL) are added. The precipitated product is filtered and dried to afford 2-(3-methoxy-phenyl)-pyrimidine-5-carboxylic acid (140 mg). MS: 231 (M+H); 1H NMR (DMSO-d6): δ 4.62 (s, 3H), 7.54 (m, 2H), 8.14 (s, 1H), 8.34 (m, 1H), 8.46 (s, 1H), 9.30 (s, 2H).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionwater (1 mL) and 1 N aqueous HCl (1.2 mL) are added
  3. filtrationThe precipitated product is filtered
  4. customdried

Sources & evidence

ORD record
ord-1d801f163d944baf9a2dfb3015b12150
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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