Reacción #60895

Ecuación de reacción

dimethylcarbamyl chloride

benzaldehyde

DIPEA

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

DIPEA

dimethylcarbamyl chloride

benzaldehyde

Intermediate 96

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

→

title compound

Rendimiento 68.0%

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

Rendimiento 68.0%

Disolventes

MeCN

MeOH

NH3

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was heated
2. 2
   Temperaturaat reflux for 24 hours
3. 3
   TemperaturaAfter heating for 5 days
4. 4
   Concentraciónthe reaction mixture was concentrated in vacuo
5. 5
   workup.ADDITIONdiluted with saturated NaHCO3 solution (5 mL)
6. 6
   Extracciónthen extracted with DCM (2×10 mL)
7. 7
   SecadoThe combined organics were dried (MgSO4)
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated in vacuo
10. 10
    Otroto give a brown residue which
11. 11
    Concentraciónthen concentrated in vacuo
12. 12
    workup.ADDITIONdiluted with 2M NaOH (8 mL)
13. 13
    Extracciónextracted with DCM (1×20 mL)
14. 14
    SecadoThe organic layer was dried (MgSO4)
15. 15
    Filtraciónfiltered
16. 16
    Concentraciónconcentrated in vacuo
17. 17
    Otrogiving a residue which
18. 18
    Otrowas purified by flash chromatography on silica (2% MeOH/DCM)

Procedimiento

N-Benzoyl-N-[2-(1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-yl]benzamide (Intermediate 96) (0.05 g) was dissolved/suspended in MeCN (5 mL), dimethylcarbamyl chloride (0.015 mL) added, then benzaldehyde (16 mg) and DIPEA (0.05 mL). The reaction mixture was heated at reflux for 24 hours then additional dimethylcarbamyl chloride (0.015 mL), benzaldehyde (16 mg) and DIPEA (0.05 mL) added. After heating for 5 days, the reaction mixture was concentrated in vacuo, diluted with saturated NaHCO3 solution (5 mL) then extracted with DCM (2×10 mL). The combined organics were dried (MgSO4), filtered and concentrated in vacuo to give a brown residue which was dissolved in MeOH (2 mL)/concentrated aqueous NH3 (2 mL). The reaction mixture was heated at 55° C. for 1 hours then concentrated in vacuo, diluted with 2M NaOH (8 mL) and extracted with DCM (1×20 mL). The organic layer was dried (MgSO4), filtered, concentrated in vacuo giving a residue which was purified by flash chromatography on silica (2% MeOH/DCM) to give the title compound as a colourless solid (0.033 g, 68%);

Fuente