Water → HCID 11137831, compound

HRID 2284813Notes

Reaction equation

HRID 2284813 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]=1

Participants

7

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

  1. stirringthe mixture was stirred at the same temperature for 2 hours
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. 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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