Sodium Acetate → 2-Chloro-7-methylthieno(3,2-d)pyrimidine

HRID 1773514Notes

Reaction equation

HRID 1773514 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.C(O)(C)C.[OH-].[OH-].[Pd+2]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 71470642,4-Dichloro-7-methylthieno(3,2-d)pyrimidine

Product 1

HCID 580562082-Chloro-7-methylthieno(3,2-d)pyrimidineYield 85.4%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,4-dichloro-7-methyl-thieno[3,2-d]pyrimidine (2.5 g), palladium hydroxide on carbon (20%, 0.5 g) and sodium acetate (2.0 g) in a mixture of ethyl acetate (40 mL) and isopropyl alcohol (5 mL) was shaken in a Parr apparatus under hydrogen atmosphere (50 PSI) overnight. The reaction mixture was filtered on a CELITE™ pad and the filtrate was evaporated under reduced pressure. The crude residue was purified by flash chromatography (DCM) to give 1.8 g of 2-chloro-7-methyl-thieno[3,2-d]pyrimidine.

Workup

  1. filtrationThe reaction mixture was filtered on a CELITE™ pad
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe crude residue was purified by flash chromatography (DCM)

Sources & evidence

ORD record
ord-bbeff7cae2c4435bb738c4a3c7dbf1c0
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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