Ethyl Acetate → HCID 69046468, compound

HRID 733174Notes

Reaction equation

HRID 733174 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][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=2)[N:6]=1)(=O)=O.[C-:23]#[N:24].[Na+].C(OCC)(=O)C>CS(C)=O>[OH:14][CH2:13][CH2:12][CH2:11][C:9]1[CH:8]=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=2)[N:6]=[C:5]([C:23]#[N:24])[N:10]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 69047064HCID 69047064, compound

Product 1

HCID 69046468HCID 69046468, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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. washwashed with water (2×200 mL)
  2. dry with materialThe organic layer was dried over sodium sulphate, solvent
  3. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-04422066d6a54adf9e1fbd8bd8564def
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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