Sodium methanethiolate → HCID 19371699, compound

HRID 1885541Notes

Reaction equation

HRID 1885541 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[CH3:15][S-:16].[Na+]>CS(C)=O.CN(C=O)C.O>[CH3:15][S:16][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

6

Reactant 2

HCID 4378561Sodium methanethiolateHCID 19371698HCID 19371698, compound

Product 1

HCID 19371699HCID 19371699, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 4-chloro-2-phenoxypyrimidine (2.00 g, 9.68 mmol) in dry DMSO (15 ml) and DMF (10 ml) at 10° C. under nitrogen was added dropwise a solution/ suspension of sodium methanethiolate (0.77 g, 9.68 mmol) in dry DMSO (15 ml) and DMF (5 ml). After approximately one hour below 15° C., the reaction mixture was diluted with water and then extracted (x3) with ether. The combined ether extracts were washed with brine and then dried. Evaporation of the solvent gave 4-methylthio-2-phenoxypyrimidine as a thick, pale yellow oil (2.00 g,87% pure by GC) which was used in the next stage without further purification.

Workup

  1. extractionextracted (x3) with ether
  2. washThe combined ether extracts were washed with brine
  3. customdried
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-fcbd79eaa0e5454a9bf26e584800147d
Source dataset
uspto-grants-1992_09
Patent number
US05145856

Reaction notes

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