Ammonium Hydroxide → 6-methoxy-5-(trifluoromethyl)-4-Pyrimidinamine

HRID 1910877Notes

Reaction equation

HRID 1910877 reaction equation
F[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([O:12][CH3:13])[N:5]=[CH:4][N:3]=1.[OH-].[NH4+:15]>C(O)CCC>[CH3:13][O:12][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH2:15])[C:7]=1[C:8]([F:11])([F:10])[F:9]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 584392514-Fluoro-6-methoxy-5-(trifluoromethyl)pyrimidine

Product 1

HCID 666076446-methoxy-5-(trifluoromethyl)-4-Pyrimidinamine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-fluoro-6-methoxy-5-(trifluoromethyl)pyrimidine (N-2) (1.10 g, 5.61 mmol) in n-butanol (4 mL) in a pressure vessel, ammonium hydroxide (5 mL) is added and the resulting mixture is stirred at 90° C. for 1 h. The mixture is allowed to cool to RT, quenched with water, and extracted with ethyl acetate (100 mL×2). The combined organic layers are washed with brine, dried over Na2SO4 and filtered. The filtrate is concentrated in vacuo to afford the product 6-methoxy-5-(trifluoromethyl)pyrimidin-4-amine (N-3) as an off-white solid. The product is used directly in the next step without further purification.

Workup

  1. temperatureto cool to RT
  2. customquenched with water
  3. extractionextracted with ethyl acetate (100 mL×2)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-f8096cb6fd8a4f8688bc4a564018f567
Source dataset
uspto-grants-2013_12
Patent number
US08604032B2

Reaction notes

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