Carbon Tetrachloride → HCID 18446622, compound

Participants

Reaction Steps

In a similar manner as described in Example 17 from N-cyclopentyl-N-(4-{3-[2-(isopropylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}-2-pyridinyl)amine (155 mg, 0.375 mmol), n-butyllithium (700 μL 1.6 M in hexanes, 1.12 mmol), and carbon tetrachloride (145 μL, 1.50 mmol) was formed 4-{7-chloro-2-[2-(cyclopentylamino)-4-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl}-N-isopropyl-2-pyrimidinamine. Flash chromatography (1:1 hexanes:ethyl acetate to 1:2 hexanes:ethyl acetate) provided sample (65 mg, 39%). Rf 0.20 (1:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 8.40 (d, 1H), 8.14–8.11 (m, 2H), 7.27 (m, 1H), 7.07 (d, 1H), 6.82 (d, 1H), 6.66 (s, 1H), 6.46 (d, 1H), 5.11 (d, 1H), 4.79 (d, 1H), 4.21 (m, 1H), 3.98 (m, 1H), 1.98 (m, 2H), 1.74–1.44 (m, 6H), 1.30 (d, 6H); MS m/z 448 (M+1).

Provenance & Evidence