Trifluoroacetic acid → 7-(Cyclopropylamino)-5-(3-hydroxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

HRID 624712Notes

Reaction equation

HRID 624712 reaction equation
[CH:1]1([N:4]([C:12]2[N:17]3[N:18]=[CH:19][C:20]([CH:21]=[O:22])=[C:16]3[N:15]=[C:14]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=3)[CH:13]=2)C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([NH:4][C:12]2[N:17]3[N:18]=[CH:19][C:20]([CH:21]=[O:22])=[C:16]3[N:15]=[C:14]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=3)[CH:13]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58196747Tert-butyl cyclopropyl(3-formyl-5-(3-hydroxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl)carbamate

Product 1

HCID 581967807-(Cyclopropylamino)-5-(3-hydroxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbaldehydeYield 34.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl cyclopropyl(3-formyl-5-(3-hydroxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl)carbamate (400 mg, 1.01 mmol) in methylene chloride (20 mL) was added TFA (10 mL). The reaction mixture was stirred at room temperature for 2 hours. The volatiles were removed by rotary evaporation and the residue was purified by silica gel chromatography (0%-40% EtOAc/hexanes) to provide 103 mg of 7-(cyclopropylamino)-5-(3hydroxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde. (35%). LCMS (M+1=295)

Workup

  1. customThe volatiles were removed by rotary evaporation
  2. customthe residue was purified by silica gel chromatography (0%-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-99ed97642426435a90d89c2cddc38850
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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