Sodium Methoxide → 4-Methoxy-6-(trifluoromethoxy)pyrimidin-2-amine

HRID 1978153

Reaction equation

HRID 1978153 reaction equation
[CH3:1][O-:2].[Na+].[NH2:4][C:5]1[N:10]=[C:9](F)[CH:8]=[C:7]([O:12][C:13]([F:16])([F:15])[F:14])[N:6]=1>CO>[NH2:4][C:5]1[N:10]=[C:9]([O:2][CH3:1])[CH:8]=[C:7]([O:12][C:13]([F:16])([F:15])[F:14])[N:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 150227162-Amino-4-fluoro-6-trifluoromethoxypyrimidine

Product 1

HCID 150227204-Methoxy-6-(trifluoromethoxy)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-2.5 °C

Procedure

2.7 g (0.015 mol) of 30% strength sodium methylate were added over the course of 15 minutes to 2.95 g (0.015 mol) of 2-amino-4-fluoro-6-trifluoromethoxypyrimidine in 50 ml of methanol while stirring at −5 to 0° C. The reaction mixture was stirred at 0° C. for 1 hour, warmed to 25° C. and then concentrated under reduced pressure, stirred with water and extracted 2× with methylene chloride. Drying and concentrating under reduced pressure resulted in 3.1 g (98% of theory) of the title compound of nD25=1.4770.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 1 hour
  2. temperaturewarmed to 25° C.
  3. concentrationconcentrated under reduced pressure
  4. stirringstirred with water
  5. extractionextracted 2× with methylene chloride
  6. customDrying
  7. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-a8328e6ade3846ff85ba8573a88571c1
Source dataset
uspto-grants-2001_05
Patent number
US06235904B1

Linked notes

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