Sodium Cyanide → 4-Benzyloxy-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile

HRID 2053094Notes

Reaction equation

HRID 2053094 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[N:12]=[C:11](S(C)(=O)=O)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:29]#[N:30].[Na+]>CS(C)=O.ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[N:12]=[C:11]([C:29]#[N:30])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 688230264-Benzyloxy-2-methanesulfonyl-6-(3-trifluoromethyl-phenyl)-pyrimidine

Product 1

HCID 588780594-Benzyloxy-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrileYield 67.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

4-Benzyloxy-2-methanesulfonyl-6-(3-trifluoromethyl-phenyl)-pyrimidine (92 mg) and sodium cyanide (22 mg) were stirred at room temperature in dimethylsulphoxide (500 μl) for 20 minutes. The reaction mixture was diluted with dichloromethane (40 ml) and washed with water (3×50 ml). Organics were separated, dried over sodium sulphate and solvent was evaporated under reduced pressure to yield crude product (86 mg) as a yellow oil. Purification by flash chromatography on silica gave product 4-benzyloxy-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile (54 mg).

Workup

  1. washwashed with water (3×50 ml)
  2. customOrganics were separated
  3. dry with materialdried over sodium sulphate and solvent
  4. customwas evaporated under reduced pressure
  5. customto yield crude product (86 mg) as a yellow oil
  6. customPurification by flash chromatography on silica

Sources & evidence

ORD record
ord-c58e4fb71de44a1c838c3cf164839a43
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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