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

HRID 1293663Notes

Reaction equation

HRID 1293663 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]pyrimidin-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-5c576964f5cb470d8d1428a62b67a9e4
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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