Methanol → 2-Methoxy-6-methylpyrimidine-4-carboxylic acid

HRID 2069383Notes

Reaction equation

HRID 2069383 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7](Cl)[N:6]=1)=[O:4].[CH3:13][OH:14]>[OH-].[Na+]>[CH3:13][O:14][C:7]1[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:10]=[C:9]([CH3:11])[N:8]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 2736835Methyl 2-chloro-6-methylpyrimidine-4-carboxylate

Product 1

HCID 190184722-Methoxy-6-methylpyrimidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of methyl-2-chloro-6-methylpyrimidine-4-carboxylate (5.0 g) in 2N aq. NaOH (67 mL) and methanol (67 mL) is stirred at rt for 24 h. Methanol is evaporated and the aq. phase is acidified with 25% aq. HCl at 0° C. A beige crystalline solid crushes out. It is filtered, rinsed with water and heptane and dried (3.0 g); LC-MS: tR=0.55 min, [M+H]+=169.01; 1H NMR (D6-DMSO): δ 2.50 (s, 3H), 3.94 (s, 3H), 7.52 (s, 1H), 13.7 (s br, 1H).

Workup

  1. customMethanol is evaporated
  2. customis acidified with 25% aq. HCl at 0° C
  3. filtrationIt is filtered
  4. washrinsed with water and heptane
  5. customdried (3.0 g)

Sources & evidence

ORD record
ord-b46050ff1e964b5ea06008e685357766
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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