N-Cyclopentyl-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine → N-cyclopentyl-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine

HRID 1296721Notes

Reaction equation

HRID 1296721 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:15]=[C:11]3[N:10]=[C:9](SC)[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Ni]>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:15]=[C:11]3[N:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 69449600N-Cyclopentyl-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine

Product 1

HCID 69447864N-cyclopentyl-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amineYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

N-Cyclopentyl-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine (300 mg, 0.92 mmol, from Example 9) was dissolved in absolute ethanol (30 mL). To this mixture was added Raney nickel (approximately 2–3 g) and the reaction was heated at reflux for 6 hours. The Raney nickel was removed by filtering the reaction mixture through a Celite pad, and the Celite was washed with ethanol (150 mL). The combined organic phase was concentrated to dryness. The resulting residue was purified by silica gel chromatography (ethyl acetate:hexane 1:1) to give 200 mg (78%) of N-cyclopentyl-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine as a yellow foam. 1H-NMR (CDCl3): δ 8.24 (s, 1H), 7.98 (m, 2H), 7.51 (m, 3H), 6.75 (s, 1H), 6.67 (d, 1H), 4.60 (m, 1H), 2.3–2.1 (m, 2H), 2.0–1.6 (m, 6H); MS m/z 280 (M+1).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 6 hours
  3. customThe Raney nickel was removed
  4. filtrationby filtering the reaction mixture through a Celite pad
  5. washthe Celite was washed with ethanol (150 mL)
  6. concentrationThe combined organic phase was concentrated to dryness
  7. customThe resulting residue was purified by silica gel chromatography (ethyl acetate:hexane 1:1)

Sources & evidence

ORD record
ord-704de2ae0d944be1b83a21273160441d
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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