Methanol → 1H-Pyrazolo[3,4-d]pyrimidin-6-amine

HRID 474377Notes

Reaction equation

HRID 474377 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]2[NH:9][N:10]=[CH:11][C:3]=12.C([O-])=O.[NH4+].CO>[Pd].O>[NH:9]1[C:4]2=[N:5][C:6]([NH2:8])=[N:7][CH:2]=[C:3]2[CH:11]=[N:10]1

Participants

6

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 117896254-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine

Product 1

HCID 196921561H-Pyrazolo[3,4-d]pyrimidin-6-amineYield 31.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture containing 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-yl amine (0.6 g, 3.54 mmol, Chembridge), 10% palladium on carbon (0.15 g), ammonium formate (1.24 g, 19.6 mmol) and methanol (20 mL) was heated at reflux for about 4 h. The reaction mixture was cooled to ambient temperature and filtered through Celite®, which was subsequently washed with additional MeOH (2×20 mL). The combined filtrates were evaporated under reduced pressure to yield a white solid. The solid was suspended in water (50 mL), filtered, and dried to afford 1H-pyrazolo[3,4-d]pyrimidin-6-yl amine (0.15 g, 31%) as a white solid. LC/MS (Table 2, Method c) Rt=2.12 min; MS m/z: 136 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for about 4 h
  3. filtrationfiltered through Celite®, which
  4. washwas subsequently washed with additional MeOH (2×20 mL)
  5. customThe combined filtrates were evaporated under reduced pressure
  6. customto yield a white solid
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-811c6dc6a9174484b5f8b962dab87c71
Source dataset
uspto-grants-2014_01
Patent number
US08637529B2

Reaction notes

Loading…