Pyridine → HCID 59608013, compound

Participants

Reaction Conditions

Reaction Steps

2-(3-chloropyrazin-2-ylamino)-1-((3aS,4R,6aR)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)ethanone (2-8) (1.2 g, 3.85 mmol, 1 equiv) was dissolved in toluene (28 mL) and the mixture was cooled to 0° C. Pyridine (3.74 mL, 46.2 mmol, 12 equiv) was added followed by TFA (2.08 mL, 26.9 mmol, 7 equiv). After 30 minutes, TFAA (3.81 mL, 26.9 mmol, 7 equiv) was added. The resulting mixture was stirred for 1 h, then was concentrated and the yellow residue was purified via flash chromatography on a silica gel column (ethyl acetate/hexanes) to yield desired 8-chloro-3-((3aS,4S,6aR)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazine (2-9) as a white solid. 1H NMR (500 MHz, CDCl3): δ 8.19 (d, J=4.6 Hz, 1H); 7.84 (d, J=4.6 Hz, 1H); 7.67 (s, 1H); 4.81 (d, J=5.2 Hz, 1H); 4.57 (dd, J=6.0, 2.6 Hz, 1H); 3.47 (s, 1H); 2.52-2.41 (m, 1H); 2.09-2.05 (m, 3H); 1.58 (s, 3H); 1.34 (s, 3H). LRMS m/z (M+H) 293.9 found, 294.1 required.

Provenance & Evidence