1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-[2-(4-Fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one

Participants

Reaction Conditions

Reaction Steps

0.975 g of the sodium salt of (±)-[4-(2-hydroxymethylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid (example 25b, step 6b), 0.534 g of 4-fluoroindoline, 0.57 ml of pyridine and 15 ml of DMF are placed in a three-necked flask. 0.9 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride is added and the mixture is stirred at ambient temperature (20° C.) for 72 hours. The reaction mixture is poured into 50 ml of water, with stirring, and then the insoluble material is filtered off through a VF filter, and washed 3 times with approximately 15 ml of water and then with 10 ml of ethyl acetate and twice approximately 5 ml of diisopropyl ether. The solid is air-dried under a hood. 2-[2-(4-Fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one is isolated (0.82 g) and characterized in the form of a pinkish solid, yield 60%.

Provenance & Evidence