Methanol → HCID 69047064, compound

HRID 733173Notes

Reaction equation

HRID 733173 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][C:16]([CH3:19])=[C:15]([CH3:20])[CH:14]=2)[N:4]=1.[CH3:21]O.O.O[O:25][S:26]([O-:28])=O.[K+]>C(OCC)(=O)C>[CH3:21][S:26]([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][C:16]([CH3:19])=[C:15]([CH3:20])[CH:14]=2)[N:4]=1)(=[O:28])=[O:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 69049724HCID 69049724, compound

Product 1

HCID 69047064HCID 69047064, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 2-methylsulfanyl-4-(3-hydroxypropyl)-6-(3,4-dimethyl-phenyl)pyrimidine (5.8 g) in a mixed solvent of methanol and water (110 ml, 10:1) was added OXONE (35 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-(3,4-dimethylphenyl)-pyrimidine as crude product. To a stirred solution of above 2-methylsulphonyl-4-(3-hydroxypropyl)-6-(3,4-dimethylphenyl)pyrimidine in dimethylsulfoxide (50 mL), was added sodium cyanide (2.9 g). The mixture was stirred at room temperature for 4 hours, then poured into ethyl acetate (300 mL) and washed with water (2×200 mL). The organic layer was dried over sodium sulphate, solvent evaporated at reduced pressure, the above residue was flashed on silica gel using Petrol/EtOAc (1:1) as eluent to give 4-(3-Hydroxy-propyl)-6-(3,4-dimethylphenyl)-pyrimidine-2-carbonitrile as product (4.8 g).

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-dc4810bc1aca4fc3a291b904d8fd8dda
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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