Cesium carbonate → HCID 118863788, compound

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Trimethylboroxine	HCID 574072	—
Reactant	3-(7-bromo-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate	HCID 118863779	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 118863788	HCID 118863788	92%

Reaction Steps

To a solution of 3-(7-bromo-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (150 mg, 0.297 mmol) in dioxane (2 mL) was added 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (112.0 mg, 0.892 mmol), Cs2CO3 (290.8 mg, 0.892 mmol) and Pd(dppf)Cl2 (20 mg, 0.0274 mmol). The reaction was heated at 150° C. (MW) for 30 min, cooled to RT then diluted with EA (5 mL) and water (5 mL). The organic layer was dried over Na2SO4 and concentrated to give 3-(1,7-dimethyl-2,4-dioxo-6-(3-(trifluoromethoxy) phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (120 mg, 91.8% yield) as a solid. LCMS: MH+ 440 and TR=1.571 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09440983B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-025f6359b7234feeb741c92b656ff1cf
Source note	uspto-grants-2016_09