反应 #88643

反应方程式

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

收率 60.0%

溶剂

dioxane

反应条件

后处理

1. 1
   其他The reaction was degassed with nitrogen (3×)
2. 2
   温度heated at 85° C. (MW) for 20 min
3. 3
   workup.ADDITIONdiluted with EA (10 mL) and water (3 mL)
4. 4
   过滤then filtered
5. 5
   浓缩The filtrate was concentrated to a residue which
6. 6
   其他was purified by chromatography
7. 7
   洗涤eluted with PE/EA (2:1)

实验过程

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.

来源