Ethanethiol → Methyl 2-chloro-6-(ethylthio)pyrimidine-4-carboxylate

HRID 2233882Notes

Reaction equation

HRID 2233882 reaction equation
[CH2:1]([SH:3])[CH3:2].[Cl:4][C:5]1[N:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7](Cl)[N:6]=1>C1COCC1.CCOC(C)=O.O>[Cl:4][C:5]1[N:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]([S:3][CH2:1][CH3:2])[N:6]=1

Participants

6

Reactant 2

HCID 6343EthanethiolHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylate

Product 1

HCID 86038397Methyl 2-chloro-6-(ethylthio)pyrimidine-4-carboxylateYield 98.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethanethiol (0.30 g, 4.8 mmol) in THF (1 ml) was added dropwise to a solution of methyl 2,6-dichloropyrimidine-4-carboxylate (1 g, 4.8 mmol), THF (8 ml) and TEA (0.49 g, 4.8 mmol) at 0° C. under nitrogen. The mixture was stirred for 2 h and slowly warmed to room temperature. The mixture was diluted with EtOAc (50 ml) and water (10 ml). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound (1.1 g).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9fa0c19478664c7f87d7290449d294c9
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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