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
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]1Participants
4
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).