Pyridine → HCID 86648186, compound

Participants

Reaction Conditions

Reaction Steps

2-(3-chloropyrazin-2-ylamino)-1-((3aS,4R,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)ethanone (1-7) (401 mg, 0.69 mmol, 1 equiv) was dissolved in toluene (5.1 mL) and cooled to 0° C. Pyridine (0.67 mL, 8.27 mmol, 12 equiv) was added followed by TFA (0.37 mL, 4.82 mmol, 7 equiv). After 30 minutes, TFAA (0.68 mL, 4.82 mmol, 7 equiv) was added. The resulting mixture was allowed to warm to 15° C. and stirred for 20 h. The reaction was diluted with toluene, washed with sodium bicarbonate, dried (MgSO4), and concentrated. The yellow residue was purified via flash chromatography on silica gel column (ethyl acetate/hexanes) to yield of 8-chloro-3-((3aS,4S,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazine (1-8) as an off-white solid. 1H NMR (500 MHz, CDCl3) δ 7.93 (d, 1H, J=3 Hz), 7.64 (d, 1H, J=3 Hz), 7.21-7.49 (m, 15H), 5.94 (br s, 2H), 5.06 (d, 1H, J=5.5 Hz), 4.98 (d, 1H, J=5.5 Hz), 4.45 (m, 2H), 3.89 (d, 1H, J=14.5 Hz), 3.76 (m, 1H), 3.71 (d, 1H, J=14.5 Hz), 1.36 (s, 3H), 1.33 (s, 3H). LRMS m/z (M+H) 563.9 found, 564.2 required.

Provenance & Evidence