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

HRID 1633493Notes

Reaction equation

HRID 1633493 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-a1e0a40749424c02b40dc4881f640cd1
Source dataset
uspto-grants-2003_01
Patent number
US06503914B1

Reaction notes

Loading…