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

HRID 1738829Notes

Reaction equation

HRID 1738829 reaction equation
[N:1]1[C:6]2[N:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=O)[NH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:14]>>[Cl:14][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 1354402774-Hydroxypyrido (2,3-d)pyrimidine

Product 1

HCID 5690394-Chloropyrido[2,3-d]pyrimidineYield 70%

Procedure

A mixture of pyrido[2,3-d]pyrimidin-4(3H)-one (1.471 g, 10 mM) and POCl3 (16 ml) is stirred for 1 h at reflux. The excess of POCl3 is removed under vacuum. Then dichloromethane and iced water is added and the mixture stirred until the black solid dissolves. The organic layer is separated, washed with bicarbonate solution, dried over Na2SO4 and then evaporated to dryness. The yellow residue is recrystallized from toluene/hexane to give almost pure title compound in 70% yield. mp 137° C.

Workup

  1. temperatureat reflux
  2. customThe excess of POCl3 is removed under vacuum
  3. additionThen dichloromethane and iced water is added
  4. stirringthe mixture stirred until the black solid
  5. dissolutiondissolves
  6. customThe organic layer is separated
  7. washwashed with bicarbonate solution
  8. dry with materialdried over Na2SO4
  9. customevaporated to dryness
  10. customThe yellow residue is recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-9e18d32c995642e18c3200afab51ea84
Source dataset
uspto-grants-1999_10
Patent number
US05965563

Reaction notes

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