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

HRID 2211433Notes

Reaction equation

HRID 2211433 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 as 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-fed04a0ceb4d4011a69766e44f8a3bec
Source dataset
uspto-grants-2006_09
Patent number
USRE039267E1

Reaction notes

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