Ethyl Acetate → 5-ethynyl-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamine
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([C:19]#[C:20][Si](C)(C)C)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.[Cl-].[NH4+]>CO.O1CCCC1>[C:19]([C:12]1[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[N:14][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[N:10][CH:11]=1)#[CH:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of N2-(3-fluorophenyl)-N4-propyl-5-((trimethylsilyl)ethynyl)pyrimidine-2,4-diamine (S1, 509 mg) in methanol (10 mL) and tetrahydrofuran (10 mL), potassium carbonate (246 mg) was added at room temperature, and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture, ethyl acetate and saturated aqueous ammonium chloride were added. The organic layer was separated, washed successively with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 94 to 60% hexane in ethyl acetate) to obtain 5-ethynyl-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamine (S2, 226 mg).
Workup
- customThe organic layer was separated
- washwashed successively with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (eluent, 94 to 60% hexane in ethyl acetate)
Sources & evidence
- ORD record
- ord-45475adcce404cc4b6715489532c7d5a
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09145415B2
Reaction notes
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