Ammonium Chloride → HCID 69925537, compound

Participants

Reaction Steps

To a solution of 4-({3-[(1S,2S)-2-hydroxycyclohexyl]-4-oxo-3,4-dihydropyrido[3,4-h]quinazolin-6-yl}methyl)benzaldehyde (Example 10, 0.035 g, 0.085 mmol) in 2 mL of THF at −50° C. was added methylmagnesium bromide (0.028 mL, 3.0 M diethyl ether solution, 0.85 mmol). After 3 h, additional methylmagnesium bromide (0.028 mL, 3.0 M diethyl ether solution, 0.85 mmol) was added. After 1 h, the mixture was treated with saturated aqueous ammonium chloride and extracted 2× with ethyl acetate. The combined organic fractions were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-5% methanol in dichloromethane to provide the title compound that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 430.0 for [M+H]+: 1H NMR (400 MHz, CDCl3) δ 9.25 (s, 1H), 8.53 (s, 1H), 8.42 (d, J=4.5 Hz, 1H), 8.23 (s, 1H), 8.01 (s, 1H), 7.25 (d, J=9.2 Hz, 2H), 7.18 (d, J=8.1 Hz, 2H), 4.88-4.84 (m, 1H), 4.56 (br s, 1H), 4.47 (s, 2H), 4.14-4.12 (m, 1H), 3.65-3.63 (m, 1H), 2.31-2.28 (m, 1H), 2.05-1.84 (m, 4H), 1.62-1.48 (m, 2H), 1.46 (d, J=6.4 Hz, 3H).

Provenance & Evidence