Chlorotrimethylsilane → Methyl 5-chloro-2-(methylthio)pyrimidine-4-carboxylate

HRID 518780Notes

Reaction equation

HRID 518780 reaction equation
Cl[Si](C)(C)[CH3:3].[Cl:6][C:7]1[C:8]([C:15]([OH:17])=[O:16])=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=1>CO.ClCCl>[Cl:6][C:7]1[C:8]([C:15]([O:17][CH3:3])=[O:16])=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=1

Participants

5

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 7257115-Chloro-2-(methylsulfanyl)pyrimidine-4-carboxylic acid

Product 1

HCID 4736921Methyl 5-chloro-2-(methylthio)pyrimidine-4-carboxylateYield 95.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

16.0 g of chloro(trimethyl)silane are added dropwise to a solution of 6.2 g of 5-chloro-2-(methylsulfanyl)pyrimidine-4-carboxylic acid 1 in 100 ml of methanol and 100 ml of dichloromethane. The mixture is stirred at ambient temperature for 20 h, and then concentrated under vacuum. The residue is taken up with water and extracted with dichloromethane. The organic phase is dried over magnesium sulfate and concentrated under vacuum so as to obtain 6.3 g of methyl 5-chloro-2-(methylsulfanyl)pyrimidine-4-carboxylate 2 in the form of a brown oil.

Workup

  1. concentrationconcentrated under vacuum
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated under vacuum so as

Sources & evidence

ORD record
ord-a1bfda7f613a4a7d9be41445376a8292
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

Loading…