Phosphorus oxychloride → HCID 89996089, compound

HRID 1480860Notes

Reaction equation

HRID 1480860 reaction equation
[CH3:1][C:2]1[C:11]2[CH:10]=[N:9][C:8]([S:12][CH3:13])=[N:7][C:6]=2[C:5](=O)[NH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:5]1[C:6]2[N:7]=[C:8]([S:12][CH3:13])[N:9]=[CH:10][C:11]=2[C:2]([CH3:1])=[CH:3][N:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 89996004HCID 89996004, compound

Product 1

HCID 89996089HCID 89996089, compoundYield 52%

Procedure

A solution of 5-methyl-2-(methylthio)pyrido[3,4-d]pyrimidin-8(7H)-one (Preparation 186, 48 mg, 0.232 mmol) in POCl3 (1.5 mL) was heated to 70° C. for 2 hours. The reaction was concentrated in vacuo and partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water and brine, dried and adsorbed on silica. The residue was purified by silica gel column chromatography eluting with 0 to 15% EtOAc in cyclohexanes to give the title compound (27 mg, 52%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompartitioned between EtOAc and saturated aqueous NaHCO3
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organic layers were washed with water and brine
  5. customdried
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 0 to 15% EtOAc in cyclohexanes

Sources & evidence

ORD record
ord-c6905748301846029cc35a564b10f951
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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