تفاعل #88643

معادلة التفاعل

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

المردود 60.0%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was degassed with nitrogen (3×)
2. 2
   درجة الحرارةheated at 85° C. (MW) for 20 min
3. 3
   workup.ADDITIONdiluted with EA (10 mL) and water (3 mL)
4. 4
   ترشيحthen filtered
5. 5
   تركيزThe filtrate was concentrated to a residue which
6. 6
   أخرىwas purified by chromatography
7. 7
   غسيلeluted with PE/EA (2:1)

الإجراء التجريبي

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.

المصدر