Reacción #63771

Ecuación de reacción

trimethylaluminum

compound

2-(2-pyridinyl)benzenesulfonamide

methyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate

HCl

→

product

Rendimiento 42.3%

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-pyridinyl)benzenesulfonamide

Rendimiento 42.3%

Disolventes

toluene

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter heating
2. 2
   Temperaturaat reflux for 4 days
3. 3
   Temperaturathe solution was cooled to 0°
4. 4
   Otrothe mixture was partitioned between methylene chloride and water
5. 5
   ConcentraciónThe organic layer was concentrated
6. 6
   Otrothe residue was chromatographed on silica gel

Procedimiento

A solution of 1.2 g of the compound from Example 2 and 1.3 g of methyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate in 50 ml of methylene chloride was stirred under nitrogen and 3.4 ml of a 2N solution of trimethylaluminum in toluene was added. After heating at reflux for 4 days, the solution was cooled to 0°, 3 ml of 2N HCl (aq.) was added, the mixture was partitioned between methylene chloride and water. The organic layer was concentrated and the residue was chromatographed on silica gel to afford 0.9 g of the product, m.p. 175°-176°. NMR (DMSO-d6)δ: 3.8 (s, 6), 6.0 (s, 1), 7.2-8.3 (m).

Fuente