Sodium Acetate → 7-Methylthieno[3,2-d]pyrimidine

HRID 1773511Notes

Reaction equation

HRID 1773511 reaction equation
Cl[C:2]1[C:3]2[S:10][CH:9]=[C:8]([CH3:11])[C:4]=2[N:5]=[CH:6][N:7]=1.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.C(O)(C)C.[OH-].[OH-].[Pd+2]>[CH3:11][C:8]1[C:4]2[N:5]=[CH:6][N:7]=[CH:2][C:3]=2[S:10][CH:9]=1

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 27775864-Chloro-7-methylthieno(3,2-d)pyrimidine

Product 1

HCID 552806237-Methylthieno[3,2-d]pyrimidineYield 61.5%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chloro-7-methyl-thieno[3,2-d]pyrimidine (2 g), palladium hydroxide on carbon (20%, 1 g) and sodium acetate (2 g) in a mixture of ethyl acetate and isopropanol (5/1, 30 mL) was shaken in a Parr apparatus under hydrogen atmosphere (50 PSI) overnight. The resulting mixture was filtered on a CELITE™ pad, the filter cake was washed with dichloromethane and the filtrate was evaporated under reduced pressure. The crude residue was purified by flash chromatography (acetone/DCM, 3/97) to afford 1 g of 7-methyl-thieno[3,2-d]pyrimidine.

Workup

  1. filtrationThe resulting mixture was filtered on a CELITE™ pad
  2. washthe filter cake was washed with dichloromethane
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe crude residue was purified by flash chromatography (acetone/DCM, 3/97)

Sources & evidence

ORD record
ord-90b32c500f9d4f0eb37c17b047918406
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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