2-Chloropyrimidine → 2-(Methylthio)-4-phenylpyrimidine

HRID 1166156Notes

Reaction equation

HRID 1166156 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1.ClC1N=CC=CN=1>CN(C=O)C.O>[CH3:1][S:2][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 744042-ChloropyrimidineHCID 6053562-Chloro-4-phenylpyrimidineHCID 4378561Sodium methanethiolate

Product 1

HCID 8175782-(Methylthio)-4-phenylpyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium methanethiolate (0.35 g) in DMF (5 ml) at 0° C. was added dropwise a solution of 2-chloro-4-phenylpyrimidine (0.86 g, prepared from 2-chloropyrimidine according to the method of D B Harden et al., J.Org.Chem., 1988, 53, 4137) in DMF (5 ml). Stirring was continued at 0° C. for 15 minutes and then the temperature was allowed to rise to room temperature. After a further 2 hours, the reaction mixture was diluted with water and then extracted with ether (×3). The combined ether extracts were washed with water, dried, filtered and evaporated to give 2-methylthio-4-phenylpyrimidine (0.76 g) as a brown solid which was used directly in the next stage.

Workup

  1. customto rise to room temperature
  2. waitAfter a further 2 hours
  3. extractionextracted with ether (×3)
  4. washThe combined ether extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-341fde3a4d57405398ba434cf19f993f
Source dataset
uspto-grants-2003_09
Patent number
US06613773B2

Reaction notes

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