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

HRID 1192443Notes

Reaction equation

HRID 1192443 reaction equation
[N:1]1[C:6]2[N:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](O)=[N: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 178518041HCID 178518041, compound

Product 1

HCID 5690394-Chloropyrido[2,3-d]pyrimidineYield 7.6%

Procedure

The Pyrido[2,3-d]pyrimidin-4-ol (3 g) in POCl3 (45 mL) was stirred at reflux for 3 hours. The excess POCl3 was removed. The residue was added 10 mL of cold water and extracted with EtOAc (2×30 mL). The combined organic layer was washed with brine and dried over sodium sulfate. After removal of solvent, it gave 4-chloropyrido[2,3-d]pyrimidine as yellow solid (0.3 g, 7.6%). 1H NMR (CDCl3, 400 MHz) δ 9.38 (br, 1H), 9.31 (s, 1H), 8.62 (d, 1H), 7.75 (m, 1H).

Workup

  1. temperatureat reflux for 3 hours
  2. customThe excess POCl3 was removed
  3. additionThe residue was added 10 mL of cold water
  4. extractionextracted with EtOAc (2×30 mL)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customAfter removal of solvent, it

Sources & evidence

ORD record
ord-225d68c2925542b692a6024f61a5278c
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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