Phosphorus oxychloride → HCID 15512586, compound

HRID 1018718Notes

Reaction equation

HRID 1018718 reaction equation
O=[C:2]1[NH:7][C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:5][C:4]2[S:14][C:15]3[CH2:20][N:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18][CH2:17][C:16]=3[C:3]1=2.P(Cl)(Cl)([Cl:28])=O>>[Cl:28][C:2]1[C:3]2[C:16]3[CH2:17][CH2:18][N:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:20][C:15]=3[S:14][C:4]=2[N:5]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 15512585HCID 15512585, compound

Product 1

HCID 15512586HCID 15512586, compound

Conditions

Temperature
90 °C

Procedure

4.1 g of 5,6,7,8-tetrahydro-4-oxo-7-ethoxycarbonyl-2-(3-pyridyl)pyrido[4′,3′:4,5]thieno[2,3-d]pyrimidine was added to 40 ml of phosphorus oxychloride, and stirred at 80 to 100° C. for 3 hours. After phosphorus oxychloride was distilled off under reduced pressure, 50 ml of water was added to the reaction residue. The reaction solution was made alkaline with an aqueous saturated solution of sodium hydrogen carbonate while cooling, and extracted with chloroform. The organic layer was washed with saturated salt water and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off. The filtrate was concentrated under reduced pressure to give 5.0 g of 5,6,7,8-tetrahydro-4-chloro-7-ethoxycarbonyl-2-(3-pyridyl)pyrido[4′,3′:4,5]thieno[2,3-d]pyrimidine.

Workup

  1. distillationAfter phosphorus oxychloride was distilled off under reduced pressure, 50 ml of water
  2. additionwas added to the reaction residue
  3. temperaturewhile cooling
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with saturated salt water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationMagnesium sulfate was filtered off
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9cdedd9bc74346dd8bc9cd6fc8f1dba8
Source dataset
uspto-grants-2002_11
Patent number
US06482948B1

Reaction notes

Loading…