Ethyl Acetate → HCID 57839121, compound

HRID 733179Notes

Reaction equation

HRID 733179 reaction equation
CS([C:5]1[N:10]=[C:9]([CH2:11][CH2:12][CH2:13][OH:14])[CH:8]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:16]=2C)[N:6]=1)(=O)=O.[C-:26]#[N:27].[Na+].C(OCC)(=O)C>CS(C)=O>[C:21]([C:17]1[CH:16]=[C:15]([C:7]2[CH:8]=[C:9]([CH2:11][CH2:12][CH2:13][OH:14])[N:10]=[C:5]([C:26]#[N:27])[N:6]=2)[CH:20]=[CH:19][CH:18]=1)([CH3:22])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 69048178HCID 69048178, compound

Product 1

HCID 57839121HCID 57839121, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirring solution of 2-methylsulphonyl-4-(3-hydroxypropyl)-6-(3-tert-butyl-methyl-phenyl)-pyrimidine (4.6 g) in DMSO (120 ml) at room temperature was added sodium cyanide (647 mg). The resulting suspension was stirred at room temperature for 3 hours. After adding ethyl acetate (200 ml), the mixture was then washed with water (100 ml×3). Organic layer was dried over MgSO4 and concentrated in vacuo, the residue was columned on silica gel using Petrol and EtOAc as eluent to give 4-(3-tert-butyl-phenyl)-6-(3-hydroxy-propyl)-pyrimidine-2-carbonitrile (4.0 g) as an oil.

Workup

  1. washthe mixture was then washed with water (100 ml×3)
  2. dry with materialOrganic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2fe62bf15b1d407aa3f1086f4997ac80
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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