3-(Methylsulfonyl)aniline hydrochloride → (3-Methanesulfonylphenyl)-[6-(4-trifluoromethylphenyl)pyrimidin-4-yl]amine

HRID 747123Notes

Reaction equation

HRID 747123 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.Cl.[CH3:19][S:20]([C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26])(=[O:22])=[O:21]>>[CH3:19][S:20]([C:23]1[CH:24]=[C:25]([NH:26][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)[N:5]=[CH:4][N:3]=2)[CH:27]=[CH:28][CH:29]=1)(=[O:21])=[O:22]

Participants

3

Reactant 2

HCID 27351793-(Methylsulfonyl)aniline hydrochlorideHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine

Product 1

HCID 10408248(3-Methanesulfonylphenyl)-[6-(4-trifluoromethylphenyl)pyrimidin-4-yl]amine

Procedure

Analogous to the procedure used to prepare Example 5(b), 4-chloro-6-(4-trifluoromethylphenyl)pyrimidine, Example 5(a), (200 mg, 0.77 mmol) and 3-methylsulphonylaniline hydrochloride (80 mg, 0.39 mmol, Acros) afforded a crude reaction product mixture, which was partitioned between EtOAc (100 mL) and 1 N NaOH (50 mL). The organic layer was washed with 1 N NaOH (50 mL), water (50 mL), satd NaCl (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (9:1 CH2Cl2/EtOAc) provided the title product as a white solid. MS (ESI, pos. ion) m/z: 394 (M+1). MP: 204-205° C.

Workup

  1. customafforded a crude
  2. customreaction product mixture, which
  3. customwas partitioned between EtOAc (100 mL) and 1 N NaOH (50 mL)
  4. washThe organic layer was washed with 1 N NaOH (50 mL), water (50 mL), satd NaCl (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel chromatography (9:1 CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-64d72d994e43474b95105f6e9fbf06ce
Source dataset
uspto-grants-2008_07
Patent number
US07396831B2

Reaction notes

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