Réaction #60911

Équation de réaction

6-[4-(3-Iodophenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine

tert-butyl carbamate

N,N′-dimethylethylenediamine

potassium phosphate

→

title compound

Rendement 9.5%

tert-Butyl {3-[5-(4-aminothieno[2,3-d]pyrimidin-6-yl)-1-methyl-1H-imidazol-4-yl]phenyl}carbamate

Rendement 9.5%

Solvants

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   Autredegassed
2. 2
   AutreThe mixture was partitioned between EtOAc and dilute aqueous NH3
3. 3
   AutreThe organic phase was dried
4. 4
   Autreevaporated
5. 5
   AutreThe residue was purified by flash chromatography on silica using a gradient of 0-100% EtOAc in DCM
6. 6
   AutreFractions were evaporated

Mode opératoire

6-[4-(3-Iodophenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine (Example 49) (43 mg) was stirred with tert-butyl carbamate (24 mg), N,N′-dimethylethylenediamine (9 mg), copper(I) iodide (10 mg), and potassium phosphate (42 mg) in 1,4-dioxane (2 mL), degassed, and heated under an inert atmosphere at 100° C. for 24 hours. The mixture was partitioned between EtOAc and dilute aqueous NH3. The organic phase was dried and evaporated. The residue was purified by flash chromatography on silica using a gradient of 0-100% EtOAc in DCM then 0-20% MeOH in DCM as eluent. Fractions were evaporated to give the title compound as a gum (4 mg, 9%);

Source