Methylhydrazine → HCID 71093641, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [4-(azetidin-1-yl)-6-chloropyrimidin-5-yl][1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanone (C6) (from Step 6, ≦0.576 mmol) in pyridine (5.0 mL) was added methylhydrazine (0.302 mL, 5.74 mmol), and the reaction was stirred at 85° C. for 4 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified via silica gel chromatography (Gradient: 0 to 30% methanol in dichloromethane) to provide the title product as a colorless oil. Yield: 200 mg, 0.556 mmol, 97% over two steps. LCMS m/z 360.5 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.21-2.30 (m, 2H), 2.34 (br s, 3H), 3.75-4.04 (br m, 4H), 3.91 (s, 3H), 3.99 (s, 3H), 7.20 (br AB quartet, JAB=8.1 Hz, ΔνAB=33 Hz, 4H), 7.67 (s, 1H), 8.32 (s, 1H).

Provenance & Evidence