Methyl Thioglycolate → HCID 86697947, compound

HRID 518781Notes

Reaction equation

HRID 518781 reaction equation
[H-].[Na+:2].Cl[C:4]1[C:5]([C:12]([O:14]C)=O)=[N:6][C:7]([S:10][CH3:11])=[N:8][CH:9]=1.[SH:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C>[CH3:21][O:20][C:18]([C:17]1[S:16][C:4]2[CH:9]=[N:8][C:7]([S:10][CH3:11])=[N:6][C:5]=2[C:12]=1[O-:14])=[O:19].[Na+:2]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 24758Sodium hydrideHCID 4736921Methyl 5-chloro-2-(methylthio)pyrimidine-4-carboxylate

Product 1

HCID 86697947HCID 86697947, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1.2 g of sodium hydride (60% in oil) are added slowly to a mixture of 6.0 g of methyl 5-chloro-2-(methylsulfanyl)pyrimidine-4-carboxylate 2 and 3.0 g of methyl sulfanylacetate in 60 ml of DMF. After 15 min at ambient temperature, the mixture is heated at 60° C. for 3 h, and then cooled to ambient temperature overnight. The resulting suspension is filtered and the solid is washed with ethyl acetate and dried under vacuum so as to obtain 3.6 g of sodium 6-(methoxycarbonyl)-2-(methylsulfanyl)thieno[3,2-d]pyrimidin-7-olate 3 in the form of a beige solid.

Workup

  1. temperaturecooled to ambient temperature overnight
  2. filtrationThe resulting suspension is filtered
  3. washthe solid is washed with ethyl acetate
  4. customdried under vacuum so as

Sources & evidence

ORD record
ord-8028f3f64359412f86ad3df3da7345a9
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

Loading…