Sodium Cyanide → HCID 58878058, compound

HRID 2053100Notes

Reaction equation

HRID 2053100 reaction equation
CS([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][OH:14])[CH:8]=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)[N:6]=1)(=O)=O.[C-:27]#[N:28].[Na+]>CS(C)=O>[OH:14][CH2:13][CH2:12][NH:11][C:9]1[CH:8]=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)[N:6]=[C:5]([C:27]#[N:28])[N:10]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 68823777HCID 68823777, compound

Product 1

HCID 58878058HCID 58878058, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-[2-Methanesulfonyl-6-(4-methoxy-3-trifluoromethyl-phenyl)-pyrimidin-4-ylamino]-ethanol (0.68 g) was dissolved in DMSO (10 ml) and sodium cyanide (0.17 g) was added. The mixture was stirred at RT for 48 hours. Mixture was partitioned between ethyl acetate (100 ml) and water (100 ml). Organics were dried and evaporated then flash chromatographed over silica (DCM-2% methanol in DCM) to afford 420 mg of 4-(2-Hydroxy-ethylamino)-6-(4-methoxy-3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile as a white solid.

Workup

  1. customMixture was partitioned between ethyl acetate (100 ml) and water (100 ml)
  2. customOrganics were dried
  3. customevaporated
  4. customflash chromatographed over silica (DCM-2% methanol in DCM)

Sources & evidence

ORD record
ord-6f10f72589e94551812e6ad74ff60c0a
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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