Sodium Bicarbonate → 5-(4-(methylsulfonyl)benzyl)-2-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Participants

Reaction Conditions

Reaction Steps

2-Chloro-5-(4-(methylsulfonyl)benzyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x38, 250 mg, 0.611 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (487 mg, 1.223 mmol), and PdCl2(dppf) (35.8 mg, 0.049 mmol) were suspended in dioxane (2.5 mL) and aqueous saturated NaHCO3 (0.5 mL). The reaction mixture was heated in a microwave at 100° C. on high absorbance for 1 hour and was subsequently diluted with ethyl acetate and washed with aqueous saturated NH4Cl (3×2 mL) and brine (3×2 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give a crude product which was loaded onto an ISCO® silica gel cartridge (4 g) and eluted using an ethyl acetatehexane gradient. The product was collected and concentrated in vacuo to afford the title compound as a yellow foam (205 mg, 52%). ESI-MS m/z [M+H]+ calc'd for C31H28N6O6S2, 645.15; found 645.5.

Provenance & Evidence