5-Azido-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde → 5-Amino-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

HRID 624832Notes

Reaction equation

HRID 624832 reaction equation
[N:1]([C:4]1[CH:9]=[C:8]([NH:10][CH:11]2[CH2:13][CH2:12]2)[N:7]2[N:14]=[CH:15][C:16]([CH:17]=[O:18])=[C:6]2[N:5]=1)=[N+]=[N-]>[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[C:8]([NH:10][CH:11]2[CH2:13][CH2:12]2)[N:7]2[N:14]=[CH:15][C:16]([CH:17]=[O:18])=[C:6]2[N:5]=1

Participants

4

Reactant 1

HCID 866546625-Azido-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

Product 1

HCID 583137635-Amino-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehydeYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The above product 5-azido-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (1.09 g, 4.46 mmol) was subjected to hydrogenation using 10% wt palladium on carbon in ethanol. The reaction was stirred under hydrogen for 6 hours. The mixture was filtered through celite and sonicated with 1:1 mixture of ethyl acetate and hexane. The light yellow solid was filtered and dried to yield 5-amino-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde as product 750 mg (85% yield). LCMS (M+1=218)

Workup

  1. filtrationThe mixture was filtered through celite
  2. customsonicated with 1:1 mixture of ethyl acetate and hexane
  3. filtrationThe light yellow solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-fd3287d797384144b105c872522746a1
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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