Sodium Hydroxide → N-(1H-benzoimidazol-2-ylmethyl)-N'-pyrimidin-2-ylmethyl-N-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine

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Reaction Steps

Using General Procedure B: To a solution of the crude aldehyde from above (332 mg) and N′-(1H-benzoimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine (49 mg, 0.14 mmol) in THF (2 mL) was added NaBH(OAc)3 (89 mg, 0.42 mmol) and the mixture was stirred at room temperature for 1.5 h. The crude material was dissolved in saturated HBr/AcOH (2 mL) and stirred at room temperature for 5 minutes. The solution was made basic with 10 N NaOH(aq) and extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (200:5:1 CH2Cl2/MeOH/NH4OH) afforded a yellow oil (44 mg).

Provenance & Evidence