Phosphorus oxychloride → 4-Chloropyrido[2,3-d]pyrimidine

HRID 2226835Notes

Reaction equation

HRID 2226835 reaction equation
[N:1]1[C:6]2[N:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[N:3][CH:2]=1.O=P(Cl)(Cl)[Cl:13]>>[Cl:13][C:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[N:7][C:6]=2[N:1]=[CH:2][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 582898Pyrido[2,3-d]pyrimidine

Product 1

HCID 5690394-Chloropyrido[2,3-d]pyrimidine

Procedure

A mixture of 17.8 g of Pyrido[2,3-d]pyrimidin(4(3H)one and 200 mL of POCl3 was stirred under reflux for one hour. Excess POCl3 was removed under vacuum, and then CH2Cl2, ice, and water were added. A black solid dissolved slowly. The organic layer was then separated, washed with aqueous NaHCO3, and dried over Na2SO4. Solvent was then removed under vacuum to leave a yellow solid, which was recrystallized from toluene/hexane. M.P. 137° dec.

Workup

  1. temperatureunder reflux for one hour
  2. customExcess POCl3 was removed under vacuum
  3. additionCH2Cl2, ice, and water were added
  4. dissolutionA black solid dissolved slowly
  5. customThe organic layer was then separated
  6. washwashed with aqueous NaHCO3
  7. dry with materialdried over Na2SO4
  8. customSolvent was then removed under vacuum
  9. customto leave a yellow solid, which
  10. customwas recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-0cbc05886a474a2a898f265815be5728
Source dataset
uspto-grants-1994_09
Patent number
US05350749

Reaction notes

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