Reacción #60833

Ecuación de reacción

potassium carbonate

2-{1-Methyl-4-phenyl-2-[(trimethylsilyl)ethynyl]-1H-imidazol-5-yl}[1,3]thiazolo[5,4-d]pyrimidin-7-amine

Intermediate 45

2-{1-Methyl-4-phenyl-2-[(trimethylsilyl)ethynyl]-1H-imidazol-5-yl}[1,3]thiazolo[5,4-d]pyrimidin-7-amine

HCl

water

→

title compound

Rendimiento 25.4%

2-(2-Ethynyl-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine

Rendimiento 25.4%

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONadded
2. 2
   Concentraciónconcentrated in vacuo
3. 3
   workup.ADDITIONthe residue diluted with water (10 mL)
4. 4
   Extracciónextracted with DCM (3×10 mL)
5. 5
   SecadoThe organic extracts were dried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   Otrothen purified by flash chromatography on silica eluting with 4% MeOH/DCM

Procedimiento

2-{1-Methyl-4-phenyl-2-[(trimethylsilyl)ethynyl]-1H-imidazol-5-yl}[1,3]thiazolo[5,4-d]pyrimidin-7-amine (Intermediate 45) (48 mg) was dissolved/suspended in MeOH (3 mL)/water (1 mL) and potassium carbonate (50 mg) added, then stirred for 90 minutes at ambient temperature. The reaction mixture was neutralised with 2M HCl, concentrated in vacuo, the residue diluted with water (10 mL) and extracted with DCM (3×10 mL). The organic extracts were dried (MgSO4), filtered, concentrated in vacuo then purified by flash chromatography on silica eluting with 4% MeOH/DCM to give the title compound as a yellow solid (10 mg, 25%);

Fuente