Trifluoroacetic acid → 7-(Cyclopropylamino)-5-(2-fluoropyridin-4-yl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

HRID 624716Notes

Reaction equation

HRID 624716 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][N:26]=[C:25]([F: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][N:26]=[C:25]([F:29])[CH:24]=3)[CH:13]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58314259Tert-butyl cyclopropyl(5-(2-fluoropyridin-4-yl)-3-formylpyrazolo[1,5-a]pyrimidin-7-yl)carbamate

Product 1

HCID 583144727-(Cyclopropylamino)-5-(2-fluoropyridin-4-yl)pyrazolo[1,5-a]pyrimidine-3-carbaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl cyclopropyl(5-(2-fluoropyridin-4-yl)-3-formylpyrazolo[1,5-a]pyrimidin-7-yl)carbamate (320 mg, 0.82 mmol) in methylene chloride (3 mL) was added TFA (3 mL). The reaction mixture was stirred at room temperature for 1.5 hours. The volatiles were removed by rotary evaporation and 1N NaOH was added to the residue to make basic. The precipitate was collected by filtration, washed with water, and dried under vacuum to provide 180 mg of 7-(cyclopropylamino)-5-(2-fluoropyridin-4-yl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (74%). LCMS (M+1=298)

Workup

  1. customThe volatiles were removed by rotary evaporation and 1N NaOH
  2. additionwas added to the residue
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-b7c91fb699744c09900b172a3e680a5e
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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