Potassium Carbonate → HCID 86659400, compound

HRID 2043449Notes

Reaction equation

HRID 2043449 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])[N:3]=1.[CH3:19][C:20]1[N:21]=[CH:22][NH:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:8][C:6]1[CH:7]=[C:2]([N:23]2[CH:24]=[C:20]([CH3:19])[N:21]=[CH:22]2)[N:3]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])[N:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 86659372(S)-4,6-Dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidin-2-amineHCID 178418800HCID 178418800, compound

Product 1

HCID 86659400HCID 86659400, compoundYield 26.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

200 mg of (S)-4,6-dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidine-2-amine and 63 mg of 4-methylimidazole were dissolved in 2 ml of dimethylformamide, and 193 mg of potassium carbonate was added thereto, and the mixture was stirred at 100° C. for 17 hours. The reaction solution was diluted with water, and then subjected to extraction with ethyl acetate. The organic layer was washed in turn with water and brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 62 mg of the objective compound as a white solid.

Workup

  1. extractionsubjected to extraction with ethyl acetate
  2. washThe organic layer was washed in turn with water and brine
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-eca902893aaa42ee8e88cff4fb02fc6b
Source dataset
uspto-grants-2013_11
Patent number
US08586591B2

Reaction notes

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