N,N-Diethylaniline → HCID 86729812, compound

HRID 1775670Notes

Reaction equation

HRID 1775670 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[S:15][CH:16]=[C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[NH:10][C:9]2=O)=[CH:4][CH:3]=1.C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:38])=O>>[Cl:38][CH:9]1[NH:10][C:11]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][S:15][C:12]=2[C:13](=[O:14])[N:8]1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 78322693HCID 78322693, compound

Product 1

HCID 86729812HCID 86729812, compoundYield 20%

Conditions

Temperature
130 °C

Procedure

3-(4-Chlorophenyl)-7-phenylthieno[3,2-d]pyrimidin-2,4(1H,3H)-dione (100 mg, 0.3 mmol), N,N-diethylaniline (0.014 ml, 0.09 mmol), and phosphoryl chloride (0.34 ml, 3.6 mmol) were placed in a reaction vessel. The mixture was heated with stirring at 130° C. overnight. After the completion of the reaction was confirmed by TLC, the reaction mixture was cooled to room temperature and separated with NaHCO3 and dichloromethane. The extracted organic layer was washed with brine, dried over anhydrous MgSO4, and filtered. The filtrate was distilled under reduced pressure. The concentrate was purified by silica gel column chromatography (EtOAc:Hex=1:5) to give 2-chloro-3-(4-chlorophenyl)-7-phenyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (22.7 mg, 0.06 mmol, 20% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customseparated with NaHCO3 and dichloromethane
  4. washThe extracted organic layer was washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. distillationThe filtrate was distilled under reduced pressure
  8. customThe concentrate was purified by silica gel column chromatography (EtOAc:Hex=1:5)

Sources & evidence

ORD record
ord-8d8c0cd1528046109bafbc3d21912390
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

Loading…