Potassium ethanethioate → HCID 86618378, compound

HRID 2098650Notes

Reaction equation

HRID 2098650 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:5]2[S:10][C:9]([CH2:11]OS(C)(=O)=O)=[CH:8][C:6]=2[N:7]=1.[C:23]([O-:26])(=[S:25])[CH3:24].[K+]>CN(C=O)C>[CH3:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[C:5]2[S:10][C:9]([CH2:11][S:25][C:23](=[O:26])[CH3:24])=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 86618377HCID 86618377, compound

Product 1

HCID 86618378HCID 86618378, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methanesulfonic acid 2-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl ester (300 mg) in DMF (8 mL) was added potassium thioacetate (113 mg). The reaction was stirred at 60° C. for 16 h and then allowed to cool to room temperature. The reaction mixture was then quenched with water (20 mL) and extracted into ethyl acetate (2×20 mL). The combined organics were washed with aqueous brine solution (3×20 mL), dried (MgSO4), concentrated and purified using column chromatography to give thioacetic acid S-(2-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl) ester as an off-white solid (210 mg).

Workup

  1. temperatureto cool to room temperature
  2. customThe reaction mixture was then quenched with water (20 mL)
  3. extractionextracted into ethyl acetate (2×20 mL)
  4. washThe combined organics were washed with aqueous brine solution (3×20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-8892d075d95b40f6b3758794bb9d29b0
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

Loading…