Cyclohexylamine → N-cyclohexyl-4-(4-(methylsulfonyl)phenyl)-6-(trifluoromethyl)pyrimidin-2-amine

HRID 1836977Notes

Reaction equation

HRID 1836977 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH:8]=[C:7]([C:21]([F:24])([F:23])[F:22])[N:6]=1)(=O)=O.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CC#N>[CH:25]1([NH:31][C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=3)[CH:8]=[C:7]([C:21]([F:24])([F:23])[F:22])[N:6]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 111764432-(Methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine

Product 1

HCID 9930803N-cyclohexyl-4-(4-(methylsulfonyl)phenyl)-6-(trifluoromethyl)pyrimidin-2-amineYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-(methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine (0.50 g, 1.31 mmol) in MeCN (10 ml) was added cyclohexylamine (0.50 ml) and the resultant solution heated under reflux for 26 h. The cooled reaction mixture was concentrated in vacuo and the residue partitioned between 2N HCl and ethyl acetate. The organic phase was separated, washed with 2N HCl then water and concentrated in vacuo to an off-white solid. This solid was crystalised from 5% AcOH/MeOH and dried in vacuo to give the title compound as a white solid (0.27 g, 52%).

Workup

  1. temperatureunder reflux for 26 h
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. customthe residue partitioned between 2N HCl and ethyl acetate
  5. customThe organic phase was separated
  6. washwashed with 2N HCl
  7. concentrationwater and concentrated in vacuo to an off-white solid
  8. customThis solid was crystalised from 5% AcOH/MeOH
  9. customdried in vacuo

Sources & evidence

ORD record
ord-1147d588bfd2439a8fa75aa94c2867ad
Source dataset
uspto-grants-2004_08
Patent number
US06780869B1

Reaction notes

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