Triphenylphosphine → HCID 21069972, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(4-fluoro-2-iodobenzyl)-3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide (0.200 g, 0.35 mmol) in acetonitrile (5 ml) was flushed with argon and then treated with N,N-diisopropylethylamine (0.25 ml, 1.4 mmol), triphenylphosphine (0.030 g), palladium(II) acetate (0.040 g). and dimethyl phosphite (0.10 ml, 1.06 mmol). The reaction mixture was then heated in a microwave oven at 120° C. for 40 min. The reaction mixture was then diluted with ethyl acetate, washed with 0.1 N hydrochloric acid, brine, dried over anhydrous magnesium sulfate and concentrated. Purification of the residue by preparative HPLC (column YMC Pack C-18, 5μ, 20×250 mm, elution gradient acetonitrile-water 0.1% trifluoroacetic acid) gave 0.120 g (64% yield) of the title material as a white solid. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.62 (6H, s, 2×CH3), 3.77 and 3.79 (3H, 2 s, OCH3), 3.95-4.05 (4H, m, 2×CH2), 4.75 (2H, d, J=4.6 Hz, NCH2), 5.32 (2H, s, OCH2), 7.22 (1H, m, aromatic), 7.3-7.35 (3H, m, aromatics), 7.38-7.42 (2H, m, aromatics), 7.48-7.54 (1H, m, aromatic), 7.55-7.62 (1H, m, aromatic), 8.54 (1H, broad t, NH). HRMS (ESI+) calculated for C25H28FN3O7P [M+H+]: 532.1649; found: 532.1642.

Provenance & Evidence