Sodium hydride → HCID 69559023, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 240 mg (10.0 mmol) of sodium hydride in 15 mL of benzene was added 783 mg (8.69 mmol) of methyl glycolate and 1.91 g (6.68 mmol) of 2-methyl-4-chloro-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidine. The mixture was heated at 60° C. and monitored by TLC (silica, 7:3 heptane-ethyl acetate) for conversion to product. After 5 days the reaction was cooled to ambient temperature and partitioned by the addition of 10 mL of 2 M sodium hydrogen sulfate and 30 mL of ethyl acetate. The aqueous phase was extracted with 10 mL of ethyl acetate. The combined organic phases were dried with sodium sulfate and concentrated to 2.5 g of oil. The residue was purified by flash chromatography (200 g silica, 7:3 heptane-ethyl acetate) to provide 1.42 g (62%) of [[2-methyl-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as a white solid. nmr (500 MHz, CDCl3) δ1.27 (t, J=7.4 Hz, 3H), 2.57 (q, J=7.4 Hz, 2H), 2.60 (s, 3H), 3.80 (s, 3H), 5.08 (s, 2H), 5.44 (s, 2H), 6.34 (s, 1H), 7.02 (d, J=7.1 Hz, 2H), 7.25 (m, 3H)

Provenance & Evidence