Reacción #1973978

Ecuación de reacción

product

1-(3-(2-aminobenzo[d]thiazol-6-yl)-5-tert-butyl-4-methoxy-phenyl)pyrimidine-2,4(1H,3H)-dione

isoamyl nitrite

→

title compound

Rendimiento 48.4%

1-(3-(benzo[d]thiazol-6-yl)-5-tert-butyl-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione

Rendimiento 48.4%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 1 h
2. 2
   Concentraciónconcentrated in vacuo
3. 3
   OtroThe crude product was purified by C-18 reverse-phase

Procedimiento

To a solution of the product from Example 53 (30 mg, 0.071 mmol) in anhydrous 1,4-dioxane (3 mL) under N2 was added isoamyl nitrite (19 μL, 0.142 mmol). The resulting mixture was stirred at reflux for 1 h, and concentrated in vacuo. The crude product was purified by C-18 reverse-phase HPLC using an acetonitrile:H2O (0.1% TFA) gradient to give the title compound (14 mg, 48%). 1H NMR (300 MHz, DMSO-d6) δ 11.42 (d, J=1.84 Hz, 1 H) 9.44 (s, 1 H) 8.34 (d, J=1.47 Hz, 1 H) 8.19 (d, J=8.46 Hz, 1 H) 7.79 (d, J=7.72 Hz, 1 H) 7.73 (dd, J=8.46, 1.84 Hz, 1 H) 7.32-7.37 (m, 2 H) 5.65 (dd, J=7.91, 2.39 Hz, 1 H) 3.24 (s, 3 H) 1.42 (s, 9 H).

Fuente