Nitrogen → HCID 21220556, compound

Participants

Reaction Conditions

Reaction Steps

5-Hydroxyindanone (3.2 g, 21.6 mmol) was dissolved in dry DMF (20 mL) in a 3-neck flask fitted with an N2 inlet and reflux condenser. The system was blanketed with N2, and 60% NaH in mineral oil (860 mg) was added slowly and in portions at 0° C. Then 2-chloropyrimidine (2.5 g) was added, the ice bath was replaced with an oil bath, and the solution was heated at 100° C. for 3 hours. This was then cooled to room temperature before removal of DMF in vacuo. To the residue was added water (50 mL), the mixture was extracted with CH2Cl2 (50 mL), and the aqueous layer extracted twice more with CH2Cl2. The organic layer was extracted with 1N NaOH (50 mL) to remove unreacted phenol and then dried with Na2SO4 and evaporated to a dark brown solid (3.6 g). The solid was extracted with EtOAc; filtration removed an insoluble precipitate. The filtrate was dried as before and evaporated to yield the product which was pure by NMR and TLC (1:1 hexane:EtOAc).

Provenance & Evidence