Pyridine → HCID 136378681, compound

Participants

Reaction Steps

A solution of 500 mg of the sodium salt of [4-(2-methylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid obtained above in 7.5 ml of DMF and 7.5 ml of pyridine is placed in a round-bottomed flask, and then 420 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 0.27 g of (S)-2-methyl-1H-indoline (CAS 22160-09-4) are added. The reaction mixture is stirred at ambient temperature for 48 h. 50 ml of water are added and the mixture is extracted with 3 times approximately 30 ml of ethyl acetate. The organic extracts are combined and successively washed with 30 ml of water, twice 30 ml of 1M hydrochloric acid solution and then 30 ml of saturated NaCl solution, dried over MgSO4 and concentrated under vacuum. The compound obtained is purified by chromatography on a 30 g Merck column (15-40 μm) at the flow rate of 30 ml/min, elution being carried out with dichloromethane/methanol from 98/2 to 95/5. The fractions containing the expected compound are combined and evaporated. (+)-2-[2-((S)-2-Methyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-methylmorpholin-4-yl)-3H-pyrimidin-4-one is isolated (237 mg), the characteristics of which are the following:

Provenance & Evidence