Sodium triacetoxyborohydride → {3-[1-(3-Benzyl-4-oxo-3,4-dihydro-pteridin-2-yl)-2-methyl-propylamino]-propyl}-carbamic acid tert-butyl ester

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Reaction Steps

Formula 108 where R2 and R3 are H; R5 is Benzyl; R6 is Isopropyl; R6′ is H; R7 is 3-Boc-amino-propyl-; X and Y are —C═ and W and Z are —N═: To a solution of dichloromethane (100 mL), 2-(1-amino-2-methyl-propyl)-3-benzyl-3H-pteridin-4-one (780 mg, 2.52 mmol) and Na(OAc)3BH (1.07 g, 5.04 mmol) was added t-butyl-N-(3-oxopropyl)-carbamate (611 mg, 3.53 mmol) at room temperature. The reaction mixture was stirred at room temperature for 3 hours, diluted with 100 mL of dichloromethane, washed with saturated sodium bicarbonate, water and brine, and dried over sodium sulfate. Concentration of the organic phase yielded the desired Boc amino product of Formula 108, {3-[1-(3-benzyl-4-oxo-3,4-dihydro-pteridin-2-yl)-2-methyl-propylamino]-propyl}-carbamic acid tert-butyl ester (1.15 g, 98%). MS (Cl) M/E: 467.3.

Provenance & Evidence