Triphenylphosphine → HCID 66780559, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(1-azidoethyl)-4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (48 mg, 0.108 mmol) in Tetrahydrofuran (THF) (1 mL) was added resin-bound triphenylphosphine (28.2 mg, 0.108 mmol) and the mixture was stirred at 60° C. overnight. The reaction was then quenched with water and stirred at 60° C. for 1 hr. The resin was removed by filtration and the filtrate was then extracted with dichloromethane. The organic solution was dried over sodium sulfate, filtered, and concentrated to provide the desired product as a brown solid. This crude material was purified on a silica gel column eluting with chloroform/(a solution of 2M ammonia in methanol) (99:1). The fractions containing product were combined, then concentrated to provide 5-(1-aminoethyl)-4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl) [1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (19 mg, 0.045 mmol, 42.0% yield). LC/MS m/z MH+=420 (theoretical), found=420.1, 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.44 (d, J=6.82 Hz, 3H) 2.48 (s, 3H) 3.53-3.63 (m, 4H) 3.72-3.85 (m, 5H) 4.02 (br. s., 1H) 5.42 (d, J=17.68 Hz, 1H) 5.78 (d, J=17.18 Hz, 1H) 6.49 (d, J=7.83 Hz, 1H) 7.07 (t, J=7.96 Hz, 1H) 7.34 (d, J=7.83 Hz, 1H)

Provenance & Evidence