Phosphorus oxychloride → 4-Chloro-7-methylthieno(3,2-d)pyrimidine

HRID 1633487Notes

Reaction equation

HRID 1633487 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(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:19])=O>>[Cl:19][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 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 1354396367-methyl-3H,4H-thieno[3,2-d]pyrimidin-4-one

Product 1

HCID 27775864-Chloro-7-methylthieno(3,2-d)pyrimidineYield 96%

Procedure

A solution of 7-methyl-3H-thieno[3,2-d]pyrimid-4-one (3, 2.9 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-chloro-7-methylthieno[3,2-d]pyrimidine (3.1 g, 96% 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-d799da2189ad4a56b8ffe96a5a6b9aca
Source dataset
uspto-grants-2003_01
Patent number
US06503914B1

Reaction notes

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