Phosphorus oxychloride → 8-Chloro-2-(methylthio)pyrido[3,4-d]pyrimidine

HRID 1480805Notes

Reaction equation

HRID 1480805 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[CH:12]=[CH:11][NH:10][C:9](=O)[C:7]=2[N:8]=1.O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:9]1[C:7]2[N:8]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=2[CH:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 899959692-(Methylthio)pyrido[3,4-d]pyrimidin-8(7H)-one

Product 1

HCID 899960258-Chloro-2-(methylthio)pyrido[3,4-d]pyrimidineYield 86%

Procedure

A solution of 2-(methylthio)pyrido[3,4-d]pyrimidin-8(7H)-one (Preparation 32, 1.47 g, 7.61 mmol) in POCl3 (70 mL) was heated to 70° C. for 18 hours. The reaction was concentrated under reduced pressure and partitioned between EtOAc and saturated aqueous NaHCO3 solution. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography eluting with 0 to 20% EtOAc in cyclohexane to give the title compound (1.39 g, 86%).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. custompartitioned between EtOAc and saturated aqueous NaHCO3 solution
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organic layers were washed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with 0 to 20% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-3a0f70e6111e4d25b846612e5603c547
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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