反应详情

A solution of 5-ethyl-N-[2-(4-methoxy-3-methylphenyl)ethyl]-N-[4-(trifluoromethoxy)benzyl]pyrimidin-2-amine (1.12 g; 2.53 mmol) in dichloromethane (70 ml) was cooled in an ice bath and treated under nitrogen with boron tribromide (1M solution in dichloromethane; 2.78 ml). Allowed to warm to rt and additional boron tribromide (2.53 ml) was added. Stirred for 2 hr and concentrated. Azeotroped 3× with MeOH, redissolved in MeOH and treated with sodium methoxide (0.14 g; 2.53 mmol). Stirred for 30 minutes and concentrated. The residue was partitioned between ethyl acetate and water. The organic phase was dried over MgSO4, filtered and concentrated to afford 4-(2-{(5-ethylpyrimidin-2-yl)[4-(trifluoromethoxy)benzyl]amino}ethyl)-2-methylphenol as a dark brown oil (0.98 g; 90% crude yield) which was used in subsequent steps without further purification.

1. concentrationconcentrated
2. customAzeotroped 3× with MeOH
3. dissolutionredissolved in MeOH
4. stirringStirred for 30 minutes
5. concentrationconcentrated
6. customThe residue was partitioned between ethyl acetate and water
7. dry with materialThe organic phase was dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated