Phosphorus oxychloride → 4-Chlorothieno[3,2-d]pyrimidine

HRID 1181268Notes

Reaction equation

HRID 1181268 reaction equation
C[C:2]1[C:6]2[N:7]=[CH:8][NH:9][C:10](=O)[C:5]=2[S:4][CH:3]=1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:10]1[C:5]2[S:4][CH:3]=[CH:2][C:6]=2[N:7]=[CH:8][N:9]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 1354396367-methyl-3H,4H-thieno[3,2-d]pyrimidin-4-one

Product 1

HCID 27358214-Chlorothieno[3,2-d]pyrimidineYield 97%

Procedure

A solution of 3H-thieno[3,2-d]pyrimid-4-one (3, 2.7 g, 18 mmol) in phosphorus oxychloride (18 mL) under N2 was heated at reflux for 1 hour. The resulting solution was allowed to cool to room temperature and then poured into a saturated aqueous solution of sodium bicarbonate to neutralize. The aqueous mixture was extracted with diethyl ether. The organic layer was washed with water followed by saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and the solvent evaporated under reduced pressure to yield 4-chlorothieno[3,2-d]pyrimidine (2.9 g, 97% yield) as a white solid.

Workup

  1. temperatureat reflux for 1 hour
  2. extractionThe aqueous mixture was extracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-39b08ac6078945a78ddc81717c6ee0ab
Source dataset
uspto-grants-2007_10
Patent number
US07285556B2

Reaction notes

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