Sodium methanethiolate → HCID 19371699, compound

HRID 129404Notes

Reaction equation

HRID 129404 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 (×3) 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 (×3) with ether
  2. washThe combined ether extracts were washed with brine
  3. customdried
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a4d79edb3b6a491eb76366509c23eac8
Source dataset
uspto-grants-1995_11
Patent number
US05468747

Reaction notes

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