Reacción #76736

Ecuación de reacción

Potassium tert-butylate

6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-ol

6-(2,4-Diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-ol

propane-2-sulfonyl chloride

→

title compound

Rendimiento 37.4%

Propane-2-sulfonic acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-yl ester

Rendimiento 37.4%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe ice bath was removed
2. 2
   workup.ADDITIONAfter 2.5 h the reaction mixture was poured into ice water
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe organic layer was washed with water and brine
5. 5
   Secadodried (MgSO4)
6. 6
   Otroevaporated

Procedimiento

Potassium tert-butylate (150 mg, 1.31 mmol) was added at 0° C. (ice bath) to a solution of 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-ol (Example 4; 293 mg, 1.09 mmol) in N,N-dimethylformamide (33 mL). After 30 min the solution was treated with propane-2-sulfonyl chloride (190 mg, 1.31 mmol), and the ice bath was removed. After 2.5 h the reaction mixture was poured into ice water, set to pH 9-10 with 25% aqueous ammonia solution, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried (MgSO4), and evaporated. Column chromatography (SiO2; CH2Cl2/MeOH/NH4OH19:1:0.05) afforded the title compound (153 mg, 37%). White solid.

Fuente