Water → HCID 11137831, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.O.C(O[CH2:15][CH3:16])(=O)C.[CH:17]([N:20](CC)C(C)C)(C)C>CS(C)=O.C(N)CC>[Cl:1][C:2]1[N:7]=[C:6]([NH:20][CH2:17][CH2:15][CH3:16])[CH:5]=[C:4]([CH3:9])[N:3]=1Participants
Procedure
To a solution of 2,4-dichloro-6-methylpyrimidine (1.00 g) in dimethyl sulfoxide (10 mL), N,N-diisopropylethylamine (1.07 mL) and propylamine (0.51 mL) were added at room temperature, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture, N,N-diisopropylethylamine (1.07 mL) and propylamine (0.51 mL) were added at room temperature, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 90 to 70% hexane in ethyl acetate) to obtain 2-chloro-6-methyl-N-propylpyrimidin-4-amine (T1, 776 mg).
Workup
- stirringthe mixture was stirred at the same temperature for 2 hours
- customThe organic layer was separated
- washwashed with saturated aqueous sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (eluent, 90 to 70% hexane in ethyl acetate)
Sources & evidence
- ORD record
- ord-5b18c7f0901c49ba8ae5c4a7570d2241
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09145415B2
Reaction notes
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