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

HRID 987514Notes

Reaction equation

HRID 987514 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]([NH:21][C:22]#[N:23])[N:3]=1.O.[C:25](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:6]([N:14]2[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]2)[N:5]=[C:4]([N:21]([C:22]#[N:23])[CH3:25])[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 857987184-chloro-2-(N-cyanoamino)-6-[(4-methyl)-piperidin-1-yl]-5-phenylpyrimidine

Product 1

HCID 223254994-chloro-2-(N-cyano-N-methylamino)-6-[(4-methyl)-piperidin-1-yl]-5-phenylpyrimidineYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-2-(N-cyanoamino)-6-[(4-methyl)-piperidin-1-yl]-5-phenylpyrimidine (0.1 g, 0.305 mmol) in dimethylformamide (4 ml) at room temperature was added water (2 ml) followed by potassium carbonate (0.084 g, 0.61 mmol) and the resulting suspension was warmed gently to afford a clear solution. To the cooled solution was then added methyl iodide (0.076 ml, 1.22 mmol) and the reaction mixture stirred at room temperature for 2.5 hours. The reaction was then quenched by the addition of saturated aqueous ammonium chloride solution (40 ml). After adding ethyl acetate (40 ml) the biphasic mixture was stirred for 5 minutes. The organic phase was then separated, washed with saturated brine (50 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 0.09 g (87% yield) of the title compound as a colorless syrup.

Workup

  1. temperaturethe resulting suspension was warmed gently
  2. customto afford a clear solution
  3. customThe reaction was then quenched by the addition of saturated aqueous ammonium chloride solution (40 ml)
  4. additionAfter adding ethyl acetate (40 ml) the biphasic mixture
  5. customThe organic phase was then separated
  6. washwashed with saturated brine (50 ml)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto afford a yellow syrup
  10. customThe crude product was chromatographed an silica gel eluting with 90:10 v/v hexane

Sources & evidence

ORD record
ord-9e12cc680e914e8f817955366d4d652d
Source dataset
uspto-grants-2003_10
Patent number
US06632821B2

Reaction notes

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