N,N'-Dimethylethylenediamine → (E)-6-(4-chlorostyryl)-3-(4-((3,3-difluoro-1-hydroxycyclobutyl)methoxy)-3-methoxyphenyl)pyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

N1,N2-dimethylethane-1,2-diamine (12 nL, 0.11 mmol) was added to a mixture of (E)-6-(4-chlorostyryl)pyrimidin-4(3H)-one Part B (25 mg, 0.11 mmol), 1-((4-bromo-2-methoxyphenoxy)methyl)-3,3-difluorocyclobutanol (38 mg, 0.12 mmol), potassium phosphate tribasic (68.4 mg, 0.322 mmol), and copper (I) iodide (20.5 mg, 0.11 mmol) in DMF (1 mL) and stirred at 100° C. overnight. The reaction was filtered and concentrated. The residue was purified using HPLC (Phen Luna Axia C18 5μ 10:90:0.1 to 90:10:0.1 MeOH—H2O-TFA) to afford the desired product (E)-6-(4-chlorostyryl)-3-(4-((3,3-difluoro-1-hydroxycyclobutyl)methoxy)-3-methoxyphenyl)pyrimidin-4(3H)-one J-3 (5.69 mg, 0.01 mmol, 10.93% yield) as a brown solid. LC/MS 475 (M+H)+, tR 1.00 min (method 5). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.17 (1H, s), 7.76 (1H, d), 7.53 (2H, d), 7.40 (2H, d), 7.08 (1H, d), 6.86-6.97 (3H, m), 6.48 (1H, s), 4.13 (2H, s), 3.89 (3H, s), 2.77-2.87 (4H, m)

Provenance & Evidence