Cyclopentylamine → N-cyclopentyl-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidin-2-amine

HRID 1836976Notes

Reaction equation

HRID 1836976 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([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26]1>CC#N>[CH:25]1([NH:30][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)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 111764432-(Methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine

Product 1

HCID 9821491N-cyclopentyl-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidin-2-amineYield 53%

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 cyclopentylamine (0.34 g) and the resultant solution heated under reflux for 18 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 a yellow oil. This oil was purified by SPE chromatography with cyclohexane:ethyl acetate (3:1) as eluant. Concentration in vacuo of the combined fractions containing pure product gave crystals which were isolated by filtration to give the title compound as a white crystalline solid (0.21 g, 53%).

Workup

  1. temperatureunder reflux for 18 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 a yellow oil
  8. customThis oil was purified by SPE chromatography with cyclohexane:ethyl acetate (3:1) as eluant
  9. concentrationConcentration in vacuo of the combined fractions
  10. additioncontaining pure product
  11. customgave crystals which
  12. customwere isolated by filtration

Sources & evidence

ORD record
ord-11f08ec5f5df49d4b11758e1014454fe
Source dataset
uspto-grants-2004_08
Patent number
US06780869B1

Reaction notes

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