Sodium Cyanide → 4-(2-Piperidin-1-yl-ethoxy)-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile

HRID 2053103Notes

Reaction equation

HRID 2053103 reaction equation
CS([C:5]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:8]=[C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[N:6]=1)(=O)=O.[C-:30]#[N:31].[Na+]>C(#N)C.CS(C)=O>[N:14]1([CH2:13][CH2:12][O:11][C:9]2[CH:8]=[C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[N:6]=[C:5]([C:30]#[N:31])[N:10]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 688229302-Methanesulfonyl-4-(2-piperidin-1-yl-ethoxy)-6-(3-trifluoromethyl phenyl)-pyrimidine

Product 1

HCID 161193874-(2-Piperidin-1-yl-ethoxy)-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrileYield 70%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-methanesulfonyl-4-(2-piperidin-1-yl-ethoxy)-6-(3-trifluoromethyl phenyl)-pyrimidine (50 mg, 0.12 mmol) and sodium cyanide (12 mg, 0.23 mmol) in acetonitrile (1.5 ml) with a few drops of DMSO was stirred at room temperature for 18 h. The solvent was removed under reduced pressure. The residue was chromatographed over silica gel (eluent: CH2Cl2 to CH2Cl2/MeOH 95/5) to yield 31 mg of the above titled compound, yield: 70%. HPLC: 99.5%.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was chromatographed over silica gel (eluent: CH2Cl2 to CH2Cl2/MeOH 95/5)

Sources & evidence

ORD record
ord-08d0ae6150904f93ae90e6a89834dc36
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

Loading…