Reacción #88643

Ecuación de reacción

3-(7-bromo-5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate

Compound 34

3-(7-bromo-5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate

3-chlorophenylboronic acid

K3PO4

→

3-(5-(4-chlorobenzyl)-7-(3-chlorophenyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate

Rendimiento 60.0%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was degassed with nitrogen (3×)
2. 2
   Temperaturaheated at 85° C. (MW) for 20 min
3. 3
   workup.ADDITIONdiluted with EA (10 mL) and water (3 mL)
4. 4
   Filtraciónthen filtered
5. 5
   ConcentraciónThe filtrate was concentrated to a residue which
6. 6
   Otrowas purified by chromatography
7. 7
   Lavadoeluted with PE/EA (2:1)

Procedimiento

To a solution of 3-(7-bromo-5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (See Compound 34, Step 4, 93 mg, 0.2 mmol), 3-chlorophenylboronic acid (62.4 mg, 0.4 mmol), aq. 2M K3PO4 (0.4 ml, 0.8 mmol) in dioxane (2 mL) was added Pd(dppf)Cl2 (10 mg, 0.013 mmol). The reaction was degassed with nitrogen (3×), heated at 85° C. (MW) for 20 min, cooled to RT, diluted with EA (10 mL) and water (3 mL) then filtered. The filtrate was concentrated to a residue which was purified by chromatography eluted with PE/EA (2:1) to give 3-(5-(4-chlorobenzyl)-7-(3-chlorophenyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (60 mg, 60% yield) as a brown solid. LCMS: MH+ 500 and TR=1.905 min.

Fuente