3-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea → 1-(4-(5-(2-Chloro-4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)phenyl)-3-methylurea

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Reaction Steps

The title compound was prepared in a manner similar to EXAMPLE 5 using 2-chloro-5-(2-chloro-4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x6, 175 mg, 0.408 mmol), (1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (225 mg, 0.815 mmol) and PdCl2(dppf) (14.91 mg, 0.020 mmol) in dioxane (5 mL) and aqueous saturated NaHCO3 (1 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.61-2.71 (m, 3H), 3.28-3.31 (m, 2H), 3.53-3.66 (m, 1H), 3.87-4.02 (m, 2H), 4.03-4.15 (m, 1H), 4.59-4.79 (m, 2H), 4.79-4.91 (m, 1H), 6.14-6.25 (m, 1H), 7.32-7.38 (m, 1H), 7.53-7.62 (m, 2H), 7.63-7.71 (m, 1H), 7.81-7.90 (m, 1H), 7.99-8.12 (m, 3H), 8.91-9.05 (m, 1H). ESI-MS m/z [M+H]+ calc'd for C25H27ClN6O4S, 543.15. found 543.5.

Provenance & Evidence