Sodium methanethiolate → HCID 59833600, compound

HRID 2375242Notes

Reaction equation

HRID 2375242 reaction equation
C[S-].[Na+].[Cl:4][C:5]1[N:10]=[C:9]([S:11]([CH3:14])(=O)=O)[N:8]=[C:7]([NH:15][CH:16]([CH3:18])[CH3:17])[C:6]=1[C:19]1[C:24]([F:25])=[CH:23][C:22]([F:26])=[CH:21][C:20]=1[F:27]>C1COCC1.CN(C=O)C.CC(OC)(C)C>[Cl:4][C:5]1[N:10]=[C:9]([S:11][CH3:14])[N:8]=[C:7]([NH:15][CH:16]([CH3:18])[CH3:17])[C:6]=1[C:19]1[C:24]([F:25])=[CH:23][C:22]([F:26])=[CH:21][C:20]=1[F:27]

Participants

6

Reactant 2

HCID 4378561Sodium methanethiolateHCID 86606162HCID 86606162, compound

Product 1

HCID 59833600HCID 59833600, compoundYield 120.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
22.5 °C

Procedure

70 mg (1.0 mmol) of sodium thiomethoxide, dissolved in 3 ml of anhydrous THF, were added to a solution of 216 mg (0.5 mmol) of [6-chloro-2-methanesulfonyl-5-(2,4,6-trifluorophenyl)pyrimidin-4-yl]isopropylamine (abbr. sulfone 2) in 2 ml of anhydrous DMF. The mixture was stirred at 20-25° C. for 16 hours and then diluted with MTBE, washed with water and dried. Distillative removal of the solvent and chromatography on silica gel gave 0.21 g of the title compound of m.p. 112-116° C.

Workup

  1. washwashed with water
  2. customdried
  3. customDistillative removal of the solvent and chromatography on silica gel

Sources & evidence

ORD record
ord-1b10cc8191e5434d808cc548673fe75e
Source dataset
uspto-grants-2008_12
Patent number
US07465735B2

Reaction notes

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