Potassium Carbonate → 7-Methoxy-2-[1-methyl-4-phenyl-2-(3-thienyl)-1H-imidazol-5-yl][1,3]thiazolo[5,4-d]pyrimidine

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Sulfuric acid magnesium salt (1:1)	HCID 24083	—
Reactant	Thiophene-3-boronic acid	HCID 581760	—
Reactant	2-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)-7-methoxy[1,3]thiazolo[5,4-d]pyrimidine	HCID 69197217	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Methanol	HCID 887	—
Solvent	Toluene	HCID 1140	—
Product	7-Methoxy-2-[1-methyl-4-phenyl-2-(3-thienyl)-1H-imidazol-5-yl][1,3]thiazolo[5,4-d]pyrimidine	HCID 69196335	82%

Reaction Steps

2-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)-7-methoxy[1,3]thiazolo[5,4-d]pyrimidine (Intermediate 43) (50 mg), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (14 mg), thiophene-3-boronic acid (17 mg) and 2M potassium carbonate (0.25 mL) were heated in toluene (5 mL)/MeOH (1 mL) at 100° C. under an inert atmosphere. After 90 minutes the reaction mixture was cooled to ambient temperature, MgSO4 added, filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with 35% EtOAc/iso-hexane gave the title compound as a colourless solid (40 mg, 82%);

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07427616B2
Source dataset	uspto-grants-2008_09
ORD ID	ord-80e7cc6287fd4e30b403aebe9cd0fd2b
Source note	uspto-grants-2008_09