Methanol → 6-Benzyl-2-methoxy-5,6,7,8-tetrahydro-[1,6]naphthyridine

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Reaction Steps

Sodium (2.49 g, 0.11 mol) was added portionwise to methanol (70 ml) and was stirred at room temperature under a nitrogen atmosphere for 30 minutes. N,N-dimethylformamide (35 ml) was added and the solution was added to 6-benzyl-2-chloro-5,6,7,8-tetrahydro-[1,6]naphthyridine (2.8 g, 10.9 mmol) (see reference WO98/30560 Example 33b). The mixture was heated at reflux under a nitrogen atmosphere for 5 days and then was evaporated under reduced pressure. The residue was purified by chromatography on silica gel using methanol in dichloromethane (gradient from 0:100 to 4:96) and the material obtained was dried under vacuum to give the title compound (2.54 g).

Provenance & Evidence