Ethyl Acetate → 4-Chloro-7-methylthieno(3,2-d)pyrimidine

HRID 1773510Notes

Reaction equation

HRID 1773510 reaction equation
[CH3:1][C:2]1[C:6]2[N:7]=[CH:8][NH:9][C:10](=O)[C:5]=2[S:4][CH:3]=1.C(OCC)(=O)C.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:10]1[C:5]2[S:4][CH:3]=[C:2]([CH3:1])[C:6]=2[N:7]=[CH:8][N:9]=1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 1354396367-methyl-3H,4H-thieno[3,2-d]pyrimidin-4-one

Product 1

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

Conditions

Temperature
100 °C

Procedure

A suspension of 7-methyl-3H-thieno[3,2-d]pyrimidin-4-one (2.1 g) in phosphorus oxychloride (10 mL) was heated at 100° C. for 1 hour. The reaction mixture was then cooled and poured into a mixture of ice-water and ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (DCM) to afford 2.0 g of 4-chloro-7-methyl-thieno[3,2-d]pyrimidine.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified by flash chromatography (DCM)

Sources & evidence

ORD record
ord-53612419a20c41bfbfb9daf3b07a76f2
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

Loading…