Cesium carbonate → 5-bromo-2-ethenylpyrimidine

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	HCID 5233012	—
Reactant	5-Bromo-2-iodopyrimidine	HCID 7006651	—
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	5-bromo-2-ethenylpyrimidine	HCID 53628664	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

5-Bromo-2-iodo-pyrimidine (2.15 g, 7.55 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (1.60 mL, 9.43 mmol) and PdCl2(dppf). (300 mg, 0.40 mmol) were dissolved in 1,4-dioxane (15 mL). A solution of Cs2CO3 (4.91 g, 15.1 mmol) in H2O (5 mL) was added and the mixture heated at 80° C. for 30 min. The reaction mixture was diluted with EtOAc (100 mL), washed with H2O, brine and separated. The organic fraction was dried and concentrated in vacuo. Purification by chromatography on silica, eluting with 5-25% EtOAc/heptane gave i (1.10 g, 79%). MS 185.11 & 187.09 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08906902B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-a621bf537cc34e7ea4b946af5ebe7a3b
Source note	uspto-grants-2014_12