Phosphorus oxychloride → HCID 89996082, compound

HRID 1480857Notes

Reaction equation

HRID 1480857 reaction equation
[CH:1]1([C:4]2[NH:15][C:14](=O)[C:7]3[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=3[CH:5]=2)[CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:14]1[C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[CH:5]=[C:4]([CH:1]2[CH2:3][CH2:2]2)[N:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 89996209HCID 89996209, compound

Product 1

HCID 89996082HCID 89996082, compoundYield 88%

Conditions

Temperature
70 °C

Procedure

6-Cyclopropyl-2-(methylthio)pyrido[3,4-d]pyrimidin-8(7H)-one (Preparation 181, 180 mg 0.77 mmole) was stirred with phosphorus oxychloride (6 mL) and the reaction was heated at 70° C. for 2 hours before concentrating in vacuo. Ethyl acetate (20 mL) was added to the residue and the solution was cooled in ice. A little ice and then sodium bicarbonate solution (10 mL) was added. The mixture was shaken thoroughly and the aqueous layer separated. The organic layer was washed with sodium bicarbonate solution (10 mL), brine (5 mL), dried and concentrated in vacuo. The residue was purified using preparative TLC eluting with 1:3 ethyl acetate:cyclohexane to afford the title compound (171 mg 88%).

Workup

  1. concentrationbefore concentrating in vacuo
  2. additionEthyl acetate (20 mL) was added to the residue
  3. temperaturethe solution was cooled in ice
  4. additionA little ice and then sodium bicarbonate solution (10 mL) was added
  5. customthe aqueous layer separated
  6. washThe organic layer was washed with sodium bicarbonate solution (10 mL), brine (5 mL)
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified
  10. washeluting with 1:3 ethyl acetate

Sources & evidence

ORD record
ord-a16b823078d442d7afbe70e40f160b52
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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