Sodium Hydroxide → HCID 9932328, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 99.5 mg (0.225 mmol) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 8.0 mL of ethanol was treated with 0.175 mL of 2 M sodium hydroxide and the mixture heated to 65° C. for 1 hour. The reaction mixture was cooled to ambient temperature and concentrated under vacuum to a white solid. The solid was dissolved in 12 mL of water and the product precipitated upon the addition of 0.40 mL of 1 M HCl. The solids were collected by filtration, washed with 10 mL of water, then dried in vacuo (40° C., 10 torr) to provide 78 mg (81%) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid as a white solid. nmr (500 MHz, dmso-d6) δ1.00 (t, J=7.4 Hz, 3H), 2.49 (s, 3H), 2.91 (q, J=7.4 Hz, 2H), 4.89 (s, 2H), 5.52 (s, 2H), 7.15 (d, J=7.2 Hz, 2H), 7.32 (m, 3H), 7.55 (s, 1H), 7.97 (s, 1H), 13.02 (bs, 1H)

Provenance & Evidence