Trimethylphosphine → HCID 89783455, compound

Participants

Reaction Steps

To a solution of (R)-8-(6-(2-azidoethyl)-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrolo-2-yl)-2-(tert-butylamino)-3-methylquinazolin-4(3H)-one (504a, 200 mg, 0.476 mmol) in THF (7 mL) at RT was added trimethylphosphine (1.0 M in THF, 0.71 mL, 0.71 mmol) followed by 3 drops of water. It was stirred at RT for 30 min then the reaction mixture was concentrated and the crude residue was purified on the ISCO Combiflash RF (24 g Redisep column, using a gradient of 0-20% 2M NH3/MeOH in DCM) affording (R)-8-(6-(2-aminoethyl)-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-2-(tert-butylamino)-3-methylquinazolin-4(3H)-one (504, 65 mg, 0.166 mmol, 35% yield) as a light yellow amorphous solid after drying under vacuum. 1H NMR (400 MHz, MeOH-d4) δ ppm 8.00 (1H, dd, J=8.0, 1.4 Hz), 7.93 (1H, dd, J=7.5, 1.5 Hz), 7.21 (1H, t, J=7.7 Hz), 6.75 (1H, s), 4.73 (1H, dd, J=7.6, 4.1 Hz), 3.56 (3H, s), 2.74-2.93 (2H, m), 2.12-2.26 (1H, m), 1.85-1.98 (1H, m), 1.57-1.67 (9H, s). m/z (ESI, +ve) 395.0 (M+1)+.

Provenance & Evidence