Sodium Iodide → HCID 131724803, compound

Participants

Reaction Conditions

Reaction Steps

The aminomethyl-pyrimidinyl ether (1.88 g, 4.94 mmol) was suspended in 14.0 mL anhydrous 2-methoxyethyl ether. Potassium carbonate was added (0.81 g, 5.85 mmol), then a catalytic amount of sodium iodide and finally 2-chloroethyl ether (0.58 g, 4.95 mmol). The reaction was heated in a 110° C. bath for 12 h under an inert atmosphere, then allowed to cool. The reaction was then partitioned between water and dichloromethane, the pH adjusted to ˜7 with ammonium chloride aqueous solution. The organics were dried with MgSO4, filtered and concentrated in vacuo. The residue (containing some 2-methoxyethyl ether) was purified by column chromatography on silica gel using 0-10% MeOH in dichloromethane eluent mixtures to provide 610 mg of desired morpholinylmethyl-pyrimidinyl ether (main fraction, 1.35 mmol, 27%) as a brown foam. Also isolated was lower Rf material, which was the de-BOC product (˜150 mg).

Provenance & Evidence