Ethanol → 2-Ethoxy-6-methyl-pyrimidine-4-carboxylic acid

HRID 2069384Notes

Reaction equation

HRID 2069384 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([CH3:11])[N:3]=1.CCN(C(C)C)C(C)C.[CH2:21]([OH:23])[CH3:22]>>[CH2:21]([O:23][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([CH3:11])[N:3]=1)[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 105352132-Chloro-6-methylpyrimidine-4-carboxylic acid

Product 1

HCID 552957052-Ethoxy-6-methyl-pyrimidine-4-carboxylic acid

Procedure

A solution of 2-chloro-6-methylpyrimidine-4-carboxylic acid (265 mg, 1.54 mmol) and Hünig's base (0.8 mL) in ethanol (1.79 mL) is stirred at 70° C. for 24 h. Ethanol is evaporated and the aq. phase is acidified with 25% aq. HCl at 0° C., concentrated and purified by prep. HPLC (X-Bridge) to give 2-ethoxy-6-methyl-pyrimidine-4-carboxylic acid (201 mg) as a yellow solid; LC-MS: tR=0.63 min, [M+H]+=183.04.

Workup

  1. customEthanol is evaporated
  2. customis acidified with 25% aq. HCl at 0° C.
  3. concentrationconcentrated
  4. custompurified by prep

Sources & evidence

ORD record
ord-8bfbd5a4199044779560e6ced6a2b659
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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