N,N-Dimethylaniline → 7-Chloro-5-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidine

HRID 268991Notes

Reaction equation

HRID 268991 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12](O)[N:11]3[N:15]=[CH:16][CH:17]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:20])=O.CN(C)C1C=CC=CC=1>>[Cl:20][C:12]1[N:11]2[N:15]=[CH:16][CH:17]=[C:10]2[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:13]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178515606HCID 178515606, compound

Product 1

HCID 210357027-Chloro-5-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidineYield 68%

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-7-ol (4.8 g, 19.5 mmol), phosphorous oxychloride (7.2 mL, 78 mmol), and N,N-dimethylaniline (0.87 mL, 7.0 mmol) was stirred at 100° C. for 2 h. The mixture was evaporated in vacuo and the residue was partitioned between water and dichloromethane. The organic phase was washed with water, dried (Na2SO4), and evaporated in vacuo. The remaining solid was crystallized from EtOAc to give 7-chloro-5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine (3.50 g, 66%) as a yellow solid; mp 151-153° C.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was partitioned between water and dichloromethane
  3. washThe organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe remaining solid was crystallized from EtOAc

Sources & evidence

ORD record
ord-de6ac57068bc4b4c827ace457910694c
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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