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

HRID 1192419Notes

Reaction equation

HRID 1192419 reaction equation
O[C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[N:8][C:4]=2[N:5]=[CH:6][N:7]=1.O=P(Cl)(Cl)[Cl:14]>>[Cl:14][C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[N:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518041HCID 178518041, compound

Product 1

HCID 5690394-Chloropyrido[2,3-d]pyrimidineYield 32%

Procedure

The solution of 4-hydroxypyrido[2,3-d]pyrimidine (2.00 g, 13.6 mmol) in POCl3 (40 mL) was refluxed for 2 hours. After cooling, the excess POCl3 was removed under vacuum. The residue was quenched with saturated NaHCO3 and extracted with ethyl acetate (3×100 mL). The organic phase was dried and concentrated. The residue was subject to column chromatography, eluted by hexane/ethyl acetate (1:1) to give 4-chloropyrido[2,3-d]pyrimidine (0.72 g, 32%). 1H NMR (CDCl3, 400 MHz) δ 9.35 (m, 1H), 9.30 (s, 1H), 8.66 (m, 1H), 7.73 (m, 1H). MS (APCI+) [M+H]+166.

Workup

  1. temperatureAfter cooling
  2. customthe excess POCl3 was removed under vacuum
  3. customThe residue was quenched with saturated NaHCO3
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. washeluted by hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-7c4902a3be2e4fa4ad671e0eaf72a667
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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