Sodium Hydroxide → HCID 178482353, compound

Participants

Reaction Steps

A solution of 2.47 g (8.62 mmol) of trans-4-[(5-Bromo-pyrimidin-2-yl)-methyl-amino]-cyclohexanol, 5.53 g (25.86 mmol) of trans-1,4-dibromo-2-butene and 0.87 g (2.57 mmol, 0.3 eq) tetrabutylammoniumhydrogensulfate in 55 ml CH2Cl2 were treated with 55 ml of 50% aqueous NaOH. The mixture was stirred at RT for 40 h, 2.76 g (12.93 mmol) of trans-1,4-dibromo-2-butene were added and stirred for further 60 h. Then CH2Cl2 was added and the layers were separated. The inorganic layer was extracted with CH2Cl2 (3×), the combined organic layers washed with brine and dried over Na2SO4. The residue was purified by column chromatography on silica gel with hexane:EtOAc (9:1 to 2:1) as eluent yielding 0.8 g (22%) trans-(2E)-[4-(4-Bromo-but-2-enyloxy)-cyclohexyl]-(5-bromo-pyrimidin-2-yl)-methyl-amine as light yellow solid, MS: 418 (MH+, 2Br).

Provenance & Evidence