Reaktion #88643

Reaktionsgleichung

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

Ausbeute 60.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was degassed with nitrogen (3×)
2. 2
   Temperaturheated at 85° C. (MW) for 20 min
3. 3
   workup.ADDITIONdiluted with EA (10 mL) and water (3 mL)
4. 4
   Filtrationthen filtered
5. 5
   EinengenThe filtrate was concentrated to a residue which
6. 6
   Sonstigewas purified by chromatography
7. 7
   Wascheneluted with PE/EA (2:1)

Vorschrift

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.

Quelle