Ethyl 7-chloro-5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine → 5-(4-Chloro-phenyl)-7-propyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 418165Notes

Reaction equation

HRID 418165 reaction equation
C([C:3]1[CH:19]=[C:6]2[N:7]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[CH:9]=[C:10](Cl)[N:5]2[N:4]=1)C.[Cl-].C([Zn+])C.C1[CH2:28][O:27]CC1.[Cl-].[CH2:30]([Zn+])[CH2:31][CH3:32].C1C[O:37]CC1.C([Mg]Cl)C>[Cl-].[Zn+2].[Cl-]>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:8]2[CH:9]=[C:10]([CH2:30][CH2:31][CH3:32])[N:5]3[N:4]=[CH:3][C:19]([C:28]([OH:27])=[O:37])=[C:6]3[N:7]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 87090264Ethyl 7-chloro-5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidineHCID 178420657HCID 178420657, compoundHCID 178420662HCID 178420662, compoundHCID 178461633HCID 178461633, compound

Product 1

HCID 666505495-(4-Chloro-phenyl)-7-propyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Subjecting ethyl 7-chloro-5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine in analogous manner to the procedure described in Example C.26, but replacing the ethylzinc chloride/THF solution by a 0.4 M propylzinc chloride/THF solution (freshly prepared from ethylmagnesium chloride and zinc chloride), the title compound was obtained. White solid. MS (ISN) 314.1 [(M−H)−]; mp 208° C.

Sources & evidence

ORD record
ord-34f4eb1891ad4ed7b9de791f94a730fd
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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