4-Hydroxycyclohexanone → HCID 59239193, compound

Participants

Reaction Conditions

Reaction Steps

and 1-ethyl-3-(4-(7-methyl-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (yf): A mixture of compound 1 (200 mg, 0.52 mmol) and 4-hydroxycyclohexanone (97.9 mg, 0.85 mmol) in a mixed solvent of DCE/DMF (3:5, 10 mL) was stirred at 70-80° C. under N2 for 20 min. The solution was cooled down to 0° C. and NaBH(OAc)3 (366.5 mg, 1.75 mmol) was added and the mixture was stirred at 70-80° C. under N2 for 1 h. The solution was concentrated under high vacuum and the residue was dissolved in DCM (10 mL) and the insoluble solid was filtered off. The mother liquor was dried over anhydrous Na2SO4 and concentrated to give the crude product which was purified by reverse-phase HPLC to give 1-ethyl-3-(4-(7-(4-hydroxy-cyclohexyl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (ye) (55.6 mg, 22%) and 1-ethyl-3-(4-(7-methyl-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (yf) (67.5 mg). 1H NMR of 41 (D6-DMSO, 400 MHz): δ 9.41 (s, 1H), 8.12 (d, J=4, 2H), 7.46 (d, J=8.8, 2H), 6.74-6.70 (m, 1H), 4.55-4.39 (m, 1H), 3.80-3.61 (m, 6H), 3.44-3.36 (m, 4H), 3.10-3.06 (m, 2H), 2.68-2.65 (m, 4H), 2.40 (s, 1H), 1.90-1.65 (m, 4H), 1.60-1.47 (m, 1H), 1.45-1.28 (m, 2H), 1.25-1.09 (m, 1H), 1.02 (t, J=7.2, 3H). LC-MS: m/z=+481 (M+H)+.

Provenance & Evidence