Sodium Iodide → HCID 131724803, compound

Temperature

110 °C

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).

1. temperatureto cool
2. customThe reaction was then partitioned between water and dichloromethane
3. dry with materialThe organics were dried with MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. additionThe residue (containing some 2-methoxyethyl ether)
7. customwas purified by column chromatography on silica gel using 0-10% MeOH in dichloromethane eluent mixtures

ORD record

ord-bd9505b73e334d98b5691abd8838282d

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07279475B2