Phosphorus oxychloride → HCID 21960234, compound

HRID 2211444Notes

Reaction equation

HRID 2211444 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:14][C:13]3[C:12](=O)[NH:11][CH:10]=[N:9][C:8]=3[CH:7]=2)=[CH:2]1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:23])=O>>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:14][C:13]3[C:12]([Cl:23])=[N:11][CH:10]=[N:9][C:8]=3[CH:7]=2)=[CH:2]1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 136184378HCID 136184378, compound

Product 1

HCID 21960234HCID 21960234, compoundYield 81%

Procedure

A solution of 6-(3-thienyl)-3H-thieno[3,2-d]pyrimid-4-one (218, 74 mg, 0.32 mmol) in phosphorus oxychloride (2 mL) under N2 was heated at reflux for 1 hour. The resulting solution was allowed to cool to room temperature, poured into a saturated aqueous solution of sodium bicarbonate to neutralize and then 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 6-(3-thienyl)-4-chlorothieno[3,2-d]pyrimidine (65 mg, 81% yield) as a yellow solid.

Workup

  1. temperatureat reflux for 1 hour
  2. extractionextracted 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-34e2d7db353e435aa16e02584e3844b6
Source dataset
uspto-grants-2006_09
Patent number
USRE039267E1

Reaction notes

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