Sodium 2-(trifluoromethyl)benzene-1-sulfinate → 2-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-[[2-(trifluoromethyl)phenyl]sulfonylmethyl]pyrimidine

HRID 2353739Notes

Reaction equation

HRID 2353739 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O-:11])=[O:10].[Na+].[Cl:15][C:16]1[N:21]=[C:20]([CH2:22]I)[CH:19]=[C:18]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]2[CH3:30])[N:17]=1>C(#N)C>[Cl:15][C:16]1[N:17]=[C:18]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]2[CH3:30])[CH:19]=[C:20]([CH2:22][S:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:1])([F:12])[F:13])(=[O:11])=[O:10])[N:21]=1

Participants

4

Reactant 2

HCID 23674774Sodium 2-(trifluoromethyl)benzene-1-sulfinate2×HCID 59380103(S)-4-(2-Chloro-6-(iodomethyl)pyrimidin-4-YL)-3-methylmorpholine

Product 1

HCID 593801482-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-[[2-(trifluoromethyl)phenyl]sulfonylmethyl]pyrimidineYield 59.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Sodium 2-(trifluoromethyl)benzenesulfinate (10.24 g, 44 mmol) was added to 2-chloro-4-(iodomethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (13 g, 36.77 mmol), in acetonitrile (500 mL) at RT under nitrogen. The resulting mixture was stirred at 80° C. for 3 hours. Additional sodium 2-(trifluoromethyl)benzenesulfinate (10.2 g, 44 mmol) was added and reaction heated at 80° C. for 1 hour. The reaction mixture allowed to cool and concentrated in vacuo. The material was dissolved in ethyl acetate (500 mL), and washed with water (200 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 40% ethyl acetate in isohexane, to give the desired material as an orange/cream solid (9.48 g).

Workup

  1. customreaction
  2. temperatureheated at 80° C. for 1 hour
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. dissolutionThe material was dissolved in ethyl acetate (500 mL)
  6. washwashed with water (200 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customto afford crude product
  11. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 40% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-e3ec402210e749e3954f5b2603ea11ba
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

Loading…