1,1,1-Trimethoxybutane → HCID 21912924, compound

Participants

Reaction Steps

Pyridine hydrochloride (0.04 g, 0.380 mmol), and trimethyl orthobutyrate (4.6 mL, 28.48 mmol) were added to a stirred solution of N4-[2-(benzyloxy)ethyl]-5,6-dimethyl-2-phenoxypyridine-3,4-diamine (6.9 g, 18.984 mmol) prepared as in Part E of Example 4 in toluene (65 mL). After the resulting solution was heated to reflux for 2 hours, the reaction was complete as determined by TLC (using 1/1 hexane/ethyl acetate), HPLC, and LC/MS. The reaction solution was then concentrated under reduced pressure, and the resulting oil was dissolved in ethyl acetate. The ethyl acetate solution was washed with brine (3×), dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting tan solids were triturated with diethyl ether, filtered off, and dried to provide 6.5862 g of pure product (by NMR and LC/MS), which was used in the next step.

Provenance & Evidence