N,N-Diethylaniline → HCID 58959477, compound

HRID 915842Notes

Reaction equation

HRID 915842 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[N:10]=[C:11]3[C:16](O)=[N:15][CH:14]=[N:13][C:12]=23)=[CH:4][CH:3]=1.C(N(CC)C1C=CC=CC=1)C.O=P(Cl)(Cl)[Cl:38]>ClCCCl>[Cl:38][C:16]1[C:11]2[C:12](=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[N:10]=2)[N:13]=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178517945HCID 178517945, compound

Product 1

HCID 58959477HCID 58959477, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of 3-(4-chlorophenyl)-2-(2-chlorophenyl)-2H-pyrazolo[4,3-d]pyrimidin-7-ol I-2A-1 b (17.55 g, 49.1 mmol) in 1,2-dichloroethane (109 ml) was added N,N-diethylaniline (32.8 ml, 206.22 mmol) followed by POCl3 (70 ml, 0.7 M). The reaction mixture was heated to reflux under nitrogen for 3 hours, and cooled to room temperature. The solvent was removed under reduced pressure. Excess POCl3 was removed by co-evaporation with toluene three times. The residue was dissolved in methylene chloride and slowly poured into vigorously stirred 1:1 CH2Cl2/saturated aqueous NaHCO3 (500 ml). Additional saturated aqueous NaHCO3 was added until the pH of the mixture was adjusted to neutral. The organic layer was separated and the aqueous layer was extracted with 200 ml methylene chloride three times. The organic layers were combined, dried (MgSO4), and concentrated. The residue was purified by SiO2-gel chromatography using 100% CH2Cl2 as the eluant to give 7-chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-2H-pyrazolo[4,3-d]pyrimidine I-2A-1c (18.4 g, 76%): MS: 375.0 (M+1)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under nitrogen for 3 hours
  3. customThe solvent was removed under reduced pressure
  4. customExcess POCl3 was removed by co-evaporation with toluene three times
  5. dissolutionThe residue was dissolved in methylene chloride
  6. additionslowly poured
  7. additionAdditional saturated aqueous NaHCO3 was added until the pH of the mixture
  8. customThe organic layer was separated
  9. extractionthe aqueous layer was extracted with 200 ml methylene chloride three times
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated
  12. customThe residue was purified by SiO2-gel chromatography

Sources & evidence

ORD record
ord-d1a32e63891b4a548a692e6d1195e56a
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

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