Ethanol → 4-(2-[2-amino-4,5,6,7-tetrahydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl]ethyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of sodium ethoxide in ethanol [prepared by reaction of 1.06 grams (44.1 mmol) of sodium hydride and 50 ml of ethanol] was combined with 4.22 grams (44.1 mmol) of guanidine HCl and then stirred at 50° C. for 20 minutes. The cooled suspension was filtered (celite) to remove NaCl and the filtrate was mixed with 2.83 grams (8.81 mmol) of 4-(2-(2-thiocarbonyl-3-carboethoxypyrrolidin-4-yl)ethyl)benzoic acid. The resulting solution was concentrated in vacuo to remove most of the alcohol and the residue was slowly heated to 90° C. while maintaining a vacuum of 10 torr. After heating 1 additional hour, the mixture was cooled and the reaction product taken up in 75 ml of water. The pH of the mixture was adjusted to 6 by addition of 6M HCl and the mixture was then filtered. The precipitate was consecutively washed with 20 ml water, 20 ml methanol, and 40 ml ether. After drying, 2.13 grams (64%) of 4-(2-[2-amino-4,5,6,7-tetrahydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl]ethyl)benzoic acid was obtained.

Provenance & Evidence