Tetrahydrofuran → [[2-methoxy-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester

Participants

Reaction Steps

To a solution of 150 mg (0.316 mmol) of [[2-(methylsulfonyl)-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy] acetic acid methyl ester in 3 mL of tetrahydrofuran and 0.5 mL of methanol was added 4 drops of 28% sodium methoxide in methanol solution. The reaction was stirred at ambient temperature for 3 hours. The reaction was quenched by the addition of 3 mL of saturated sodium bicarbonate solution and the phases separated. The organic phase was dried with sodium sulfate and concentrated to a yellow solid. The solid was purified by flash chromatography (5.0 g silica, ethyl acetate) to provide 41 mg of [[2-methoxy-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as an off white solid. nmr (500 MHz, CDCl3) δ1.11 (t, J=7.5 Hz, 3H), 2.90 (q, J=7.5 Hz, 2H), 3.77 (s, 3H), 3.96 (s, 3H), 5.04 (s, 2H), 5.43 (s, 2H), 5.74 (s, 1H), 6.58 (s, 1H), 7.16 (d, J=7.0 Hz, 2H), 7.29 (m, 3H)

Provenance & Evidence