Hydrochloric Acid → 4-[2-(3-Nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidinamine

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Reaction Conditions

Reaction Steps

3-[2-(Methylsulfinyl)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine (1.5 g, 3.9 mmol) was dissolved in aniline (5 mL). The dark mixture was heated at 100° C. for 5 h. The mixture was cooled and EtOAc (20 mL) and 1N HCl (10 mL) was added. The aqueous layer was extracted with EtOAc (20 mL) and the organic extracts combined, washed with 1N HCl, (15 mL), brine (10 mL), dried over MgSO4 and filtered. The organic solvent was removed in vacuo. The crude material was purified by silica gel chromatography (30-50% EtOAc/hexanes) to give the titled product (830 mg, 52% yield). 1H NMR (400 MHz, d6-DMSO) δ 6.58 (d, 1H, J=5.3 Hz), 6.98 (m, 1H), 7.05 (m, 1H), 7.19 (brs, 1H), 7.28-7.36 (m, 3H), 7.57-7.63 (m, 3H), 8.00 (m, 1H), 8.25-8.31 (m, 3H), 8.54 (m, 1H), 8.69 (m, 1H); ES-LC/MS: m/z (M+H)=409.

Provenance & Evidence