Methanol → HCID 69046386, compound

HRID 733160Notes

Reaction equation

HRID 733160 reaction equation
CS[C:3]1[N:8]=[C:7]([CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[N:4]=1.[CH3:23]O.O.O[O:27][S:28]([O-:30])=O.[K+]>C(OCC)(=O)C>[CH3:23][S:28]([C:3]1[N:8]=[C:7]([CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=2)[N:4]=1)(=[O:30])=[O:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 69050422HCID 69050422, compound

Product 1

HCID 69046386HCID 69046386, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 2-methylsulfanyl-4-(3-hydroxypropyl)-6-(3-trifluoromethyl-phenyl)pyrimidine (7.8 g) in a mixed solvent of methanol and water (200 ml, 10:1) was added OXONE (34 g). The mixture was stirred at room temperature for 3 hours, then, diluted with ethyl acetate (500 ml). The mixture was washed with water (3×500 ml). Organic layer dried over sodium sulphate, solvent removed under reduced pressure to give 2-methanesulphonyl-4-(3-hydroxypropyl)-6-(3-trifluoromethylphenyl)-pyrimidine (8.9 g) as crude product which was used for next step without further purification. 1H NMR (CDCl3): δ 8.3-8.4 (m, 2H), 7.8-7.87 (m, 2H), 7.68 (dd, 1H), 3.77 (t, 2H), 3.43 (s, 3H), 3.10 (t, 2H), 2.10 (m, 2H).

Workup

  1. washThe mixture was washed with water (3×500 ml)
  2. dry with materialOrganic layer dried over sodium sulphate, solvent
  3. customremoved under reduced pressure

Sources & evidence

ORD record
ord-afb449bdf58b4946ba2702b88490ec19
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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