Phosphorus oxychloride → HCID 59662442, compound

HRID 1483814Notes

Reaction equation

HRID 1483814 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[N:11][N:12]3[CH:17]=[CH:16][C:15](=O)[NH:14][C:13]=23)[CH:6]=[CH:7][CH:8]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:15]1[CH:16]=[CH:17][N:12]2[N:11]=[CH:10][C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:20])([F:19])[F:1])[CH:4]=3)=[C:13]2[N:14]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136368657HCID 136368657, compound

Product 1

HCID 59662442HCID 59662442, compoundYield 67%

Conditions

Temperature
107 °C

Procedure

A mixture of 3-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-5(4H)-one (2.07 g, 7.41 mmol) and POCl3 (6.91 ml, 74.1 mmol) was heated to 107° C. The heating was continued for 16 hours. The reaction mixture was cooled to RT and the POCl3 removed in vacuo to give a waxy solid. The solid was triturated multiple times with Et2O and the Et2O layers were combined and rotovaced. The resulting residue was taken up in DCM and washed with saturated aqueous NaHCO3, dried over Na2SO4 and concentrated in vacuo to give 5-chloro-3-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine (1.47 g, 67% yield) as a brown solid.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customthe POCl3 removed in vacuo
  3. customto give a waxy solid
  4. customThe solid was triturated multiple times with Et2O
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa40e871ee19460b889a7da1a0ba853e
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

Loading…