Ammonium Hydroxide → 6-methoxy-5-(trifluoromethyl)-4-Pyrimidinamine
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureto cool to RT
- customquenched with water
- extractionextracted with ethyl acetate (100 mL×2)
- washThe combined organic layers are washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationThe filtrate is concentrated in vacuo
Sources & evidence
- ORD record
- ord-0b9966ce049b46f499fd2f92d908cadc
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181221B2
Reaction notes
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