Benzylamine → N-benzyl-4-(4-(methylsulfonyl)phenyl)-6-(trifluoromethyl)pyrimidin-2-amine

HRID 1836989Notes

Reaction equation

HRID 1836989 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.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC#N>[CH3:20][S:17]([C:14]1[CH:15]=[CH:16][C:11]([C:9]2[CH:8]=[C:7]([C:21]([F:24])([F:23])[F:22])[N:6]=[C:5]([NH:32][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:10]=2)=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 111764432-(Methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine

Product 1

HCID 9931215N-benzyl-4-(4-(methylsulfonyl)phenyl)-6-(trifluoromethyl)pyrimidin-2-amineYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-(Methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine (0.10 g, 0.26 mmol) in MeCN (4 ml) was added benzylamine (5 eq) and the resultant solution heated under reflux for 24 h. The cooled reaction mixture was concentrated in vacuo and purified by SPE chromatography with cyclohexane:ethyl acetate (3:1). Concentration in vacuo of the combined fractions containing pure product gave the title compound as a white solid (0.090 g, 80%).

Workup

  1. temperatureunder reflux for 24 h
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. custompurified by SPE chromatography with cyclohexane:ethyl acetate (3:1)
  5. concentrationConcentration in vacuo of the combined fractions
  6. additioncontaining pure product

Sources & evidence

ORD record
ord-cc92764e2ade41dda8c8e7b4e5aa067e
Source dataset
uspto-grants-2004_08
Patent number
US06780870B2

Reaction notes

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