Phosphorus oxychloride → 7-Chloro-2-(methylthio)pyrido[2,3-d]pyrimidine

HRID 523070Notes

Reaction equation

HRID 523070 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10](=O)[NH:9][C:7]=2[N:8]=1.O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:10]1[CH:11]=[CH:12][C:6]2[CH:5]=[N:4][C:3]([S:2][CH3:1])=[N:8][C:7]=2[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12347632-(methylthio)pyrido(2,3-d)pyrimidin-7(8H)-one

Product 1

HCID 221346737-Chloro-2-(methylthio)pyrido[2,3-d]pyrimidineYield 13%

Conditions

Temperature
80 °C

Procedure

A suspension of 2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (297 mg, 1.54 mmol) in POCl3 (6 mL) was stirred under argon at 80° C. for 16 hours. The solution was cooled, and the resulting precipitate was filtered and washed with EtOAc to afford the title compound (43 mg, 13%). The filtrate was diluted with EtOAc, washed with NaHCO3 and dried with Na2SO4. After removal of the solvent, a second crop was obtained (154 mg, 48%).

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with EtOAc

Sources & evidence

ORD record
ord-2e8d445c13084abf8e1046adcc1f17c1
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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