Ethyl Acetate → 4-chloro-2-(N-cyano-N-methylamino)-6-[(4-methyl)-piperidin-1-yl]-5-phenylpyrimidine

HRID 1766588Notes

Reaction equation

HRID 1766588 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([N:14]2[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]2)[N:5]=[C:4](S(C)(=O)=O)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:31][NH:32][C:33]#[N:34].C(OCC)(=O)C>CN(C)C=O.O>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([N:14]2[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]2)[N:5]=[C:4]([N:32]([C:33]#[N:34])[CH3:31])[N:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 119415MethylcyanamideHCID 223254954-Chloro-6-[(4-methyl)-piperidin-1-yl]-2-methylsulfonyl-5-phenyl-pyrimidine

Product 1

HCID 223254994-chloro-2-(N-cyano-N-methylamino)-6-[(4-methyl)-piperidin-1-yl]-5-phenylpyrimidineYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-6-[(4-methyl)-piperidin-1-yl]-2-methylsulfonyl-5-phenyl-pyrimidine (0.5 g, 1.37 mmol) in dimethylformamide (6 ml) was added potassium carbonate (0.38 g, 2.73 mmol) followed by methyl cyanamide (0.31 g, 5.47 mmol). After stirring the reaction mixture at room temperature for 19 hours the reaction mixture was diluted with water (75 ml), and extracted with ethyl acetate (75 ml). The organic phase was washed with water (75 ml), followed by saturated brine (75 ml), dried over magnesium sulfate and concentrated in vacuo to afford a yellow syrup. The crude product was chromatographed an silica gel eluting with 90:10 v/v hexane: ethyl acetate to afford 0.39 g (84% yield) of the title compound as a colorless syrup.

Workup

  1. extractionextracted with ethyl acetate (75 ml)
  2. washThe organic phase was washed with water (75 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford a yellow syrup
  6. customThe crude product was chromatographed an silica gel eluting with 90:10 v/v hexane

Sources & evidence

ORD record
ord-e38caa02b13c4918b4eb0f4bd4a82530
Source dataset
uspto-grants-2007_06
Patent number
US07230104B2

Reaction notes

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