反应详情

To a chilled solution (ice bath) of 2-(ethoxymethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (2.0 g, 6.69 mmol, prepared according to the general methods of Example 148 using 2-methylpropan-1-amine in lieu of 1-amino-2-methylpropan-2-ol) in dichloromethane (50 mL) was added boron tribromide (20 mL, 1M solution in dichloromethane). The mixture turned light purple and was stirred at ambient temperature for 44 hours. The reaction was quenched with methanol (20 mL) and aqueous hydrochloric acid (6N, 10 mL). After stirring for 4 hours, the pH was adjusted to 10 by the addition of aqueous sodium hydroxide (50%). Dichloromethane (50 mL) was added with stirring and the layers were separated. The aqueous fraction was extracted with chloroform (2×250 mL). The combined organic fractions were concentrated to provide 1.4 g of [4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methanol as a white powder, mp 226-228° C.

1. customThe reaction was quenched with methanol (20 mL) and aqueous hydrochloric acid (6N, 10 mL)
2. stirringAfter stirring for 4 hours
3. additionthe pH was adjusted to 10 by the addition of aqueous sodium hydroxide (50%)
4. additionDichloromethane (50 mL) was added
5. stirringwith stirring
6. customthe layers were separated
7. extractionThe aqueous fraction was extracted with chloroform (2×250 mL)
8. concentrationThe combined organic fractions were concentrated