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

HRID 1784551Notes

Reaction equation

HRID 1784551 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][C:17](C([O-])=O)=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:23])=O.CN(C)C1C=CC=CC=1>>[Cl:23][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 178524812HCID 178524812, compound

Product 1

HCID 210357027-Chloro-5-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidineYield 85.8%

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(4-chloro-phenyl)-7-hydroxy-pyrazolo[1,5-a]pyrimidine-3-carboxylate (9.53 g, 0.03 mol), phosphorous oxychloride (11.0 mL, 0.12 mol), and N,N-dimethylaniline (1.3 mL, 0.01 mol) was stirred for 2 h at 100° C. 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 ethyl acetate/hexane to give 7-chloro-5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine (6.80 g, 67%). Pale-yellow solid, MS (ISP) 336.0 [(M+H)+]; mp 133-135° 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 ethyl acetate/hexane

Sources & evidence

ORD record
ord-3f9e7581880447a5a2ed0b09b5cf30a9
Source dataset
uspto-grants-2009_03
Patent number
US07504404B2

Reaction notes

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