Hydrochloric Acid → 6-(Methoxymethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylic acid

HRID 1426316Notes

Reaction equation

HRID 1426316 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].BrC[C:9]1[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]=[C:11]([C:19]([O:21][CH2:22]C)=O)[CH:10]=1.Cl>CO.O>[CH3:22][O:21][CH2:19][C:11]1[N:12]=[C:13]([C:15]([F:18])([F:16])[F:17])[N:14]=[C:9]([C:1]([OH:2])=[O:4])[CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 58431340Ethyl 6-(bromomethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate

Product 1

HCID 696732866-(Methoxymethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (1.2 g, 8.7 mmol) was added to a solution of ethyl 6-(bromomethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate (0.65 g, 1.2 mmol, prepared in the manner outlined in Example 47, Step A) in methanol (10 mL). After stirring for 2 hours, the reaction was then treated with 1N HCl to achieve pH 4, was diluted with water and extracted with six portions of 10% isopropanol in chloroform. The combined extracts were dried over sodium sulfate and concentrated to afford product as an oil which was used without further purification (0.25 g, 88%). 1H NMR (300 MHz, CDCl3) δ 8.48 (s, 1H), 4.74 (s, 2H), 3.58 (s, 3H); LCMS (M+H)+: 237.1.

Workup

  1. customprepared in the manner
  2. extractionextracted with six portions of 10% isopropanol in chloroform
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customto afford product as an oil which
  6. customwas used without further purification (0.25 g, 88%)

Sources & evidence

ORD record
ord-e082c98a6d074afebb141fe3d2e39f9c
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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