Phosphorus oxychloride → 7-Bromo-4-chlorothieno[3,2-d]pyrimidine

HRID 2211439Notes

Reaction equation

HRID 2211439 reaction equation
[Br: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(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:19])=O>>[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([Cl:19])[C:5]=2[S:4][CH:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 1357437127-Bromothieno(3,2-d)pyrimidin-4-ol

Product 1

HCID 166552667-Bromo-4-chlorothieno[3,2-d]pyrimidineYield 82%

Procedure

A solution of 7-bromo-3H-thieno[3,2-d]pyrimid-4-one (126, 0.94 g, 4.1 mmol) in phosphorus oxychloride (4 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 ethyl acetate. 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 7-bromo-4-chlorothieno[3,2-d]pyrimidine (0.83 g, 82% yield) as a yellow solid.

Workup

  1. temperatureat reflux for 1 hour
  2. extractionThe aqueous mixture was extracted with ethyl acetate
  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-867ac4ad339d4d5ba9c5951f2f52e8fb
Source dataset
uspto-grants-2006_09
Patent number
USRE039267E1

Reaction notes

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