Phosphorus oxychloride → 4-(4-Chloro-5-pyrimidinyl)-o-phenylene diacetate

HRID 1755858Notes

Reaction equation

HRID 1755858 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12](=O)[NH:13][CH:14]=[N:15][CH:16]=2)=[CH:7][C:6]=1[O:18][C:19](=[O:21])[CH3:20])(=[O:3])[CH3:2].P(Cl)(Cl)([Cl:24])=O>>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([Cl:24])=[N:13][CH:14]=[N:15][CH:16]=2)=[CH:7][C:6]=1[O:18][C:19](=[O:21])[CH3:20])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 218053924-(3,4-Dihydro-4-oxo-5-pyrimidinyl)-o-phenylene diacetate

Product 1

HCID 218054064-(4-Chloro-5-pyrimidinyl)-o-phenylene diacetate

Conditions

Temperature
100 °C

Procedure

4-(3,4-Dihydro-4-oxo-5-pyrimidinyl)-o-phenylene diacetate (194 mg) (0.67 mmol) are added to 5 ml of phosphorus oxychloride. After stirring at 100° C. for 6 hours the mixture is concentrated in a vacuum at 40° C. The residue is dissolved in dichloromethane/methanol (99:1 v/v) and the solution is washed with water. The solution is dried over sodium sulphate and concentrated. The residue is crystallized using ethanol. The beige crystals are filtered off under suction, washed with petroleum ether and dried in a high vacuum at room temperature. There are obtained 90 mg of 4-(4-chloro-5-pyrimidinyl)-o-phenylene diacetate of m.p. 108° C.

Workup

  1. concentrationis concentrated in a vacuum at 40° C
  2. dissolutionThe residue is dissolved in dichloromethane/methanol (99:1 v/v)
  3. washthe solution is washed with water
  4. dry with materialThe solution is dried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue is crystallized
  7. filtrationThe beige crystals are filtered off under suction
  8. washwashed with petroleum ether
  9. customdried in a high vacuum at room temperature

Sources & evidence

ORD record
ord-b421f8e7a7f44dcdb012d8e53b99d51e
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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