4-(Methylsulfonyl)benzyl Bromide → HCID 60197661, compound

Participants

Reaction Steps

To a solution of 5-(5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)pyrimidin-2-amine (EXAMPLE 1, 70.2 mg, 0.246 mmol) in DMSO (1.2 mL) was added sodium tert-butoxide (28.4 mg, 0.295 mmol). The resulting mixture was stirred at room temperature for 5 minutes after which 1-(bromomethyl)-4-(methylsulfonyl)benzene (0.5 mL, 0.271 mmol) was added dropwise. The resulting brown solution was stirred at room temperature for 2 hours. The reaction mixture was quenched with aqueous saturated NH4Cl, diluted with ethyl acetate, and washed with aqueous saturated NH4Cl (3×10 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The product was purified by LC/MS and the pure fractions were combined and lyophilized to give a yellow solid (4.6 mg, 4%). The product's regiochemistry was confirmed by 2D NOESY. 1H NMR (400 MHz, DMSO-d6) δ 3.16-3.25 (m, 7 H), 3.44-3.46 (m, 1 H), 3.53-3.57 (m, 1 H), 3.80-3.97 (m, 1 H), 3.98-4.03 (m, 1 H), 4.65 (s, 2 H), 4.76-4.80 (d, 1 H), 7.37 (s, 1 H), 7.42 (br s, 2 H), 7.61-7.63 (d, J=8.0 Hz, 2 H) 7.91-7.93 (d, J=8.0 Hz, 2 H), 9.00 (s, 2 H). ESI-MS m/z [M+H]+ calc'd for C21H23N7O3S, 454.16; found 454.4.

Provenance & Evidence