Cesium carbonate → 1-(2-Hydroxyethyl)-3-(5-(2-(2-hydroxypropan-2-yl)pyrimidin-5-yl)-7-(pyridin-2-yl)benzo[d]thiazol-2-yl)urea

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]propan-2-ol	HCID 66520340	—
Reactant	[2-(2-Hydroxyethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]trifluoromethanesulfonate	HCID 86696902	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	1-(2-Hydroxyethyl)-3-(5-(2-(2-hydroxypropan-2-yl)pyrimidin-5-yl)-7-(pyridin-2-yl)benzo[d]thiazol-2-yl)urea	HCID 71765340	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of iii (165 mg, 0.626 mmol) in 1,4-dioxane (12 mL) was added ii (193 mg, 0.417 mmol) and PdCl2(dppf) (34 mg, 0.042 mmol). A solution of Cs2CO3 (410 mg, 1.30 mmol) in H2O (3 mL) was added, the reaction vessel sealed, then evacuated/purged with argon (×3). The mixture was then heated under microwave irradiation at 100° C. for 30 min. LCMS analysis indicated complete conversion. The mixture was diluted with EtOAc (100 mL), washed with H2O, brine, then separated and dried (Na2SO4). The organic fraction was concentrated in vacuo. Purification by chromatography on silica, eluting with 0-10% MeOH/EtOAc followed by additional chromatography on silica, eluting with 0-10% MeOH/DCM afforded Compound 5 (9 mg, 5%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08906902B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-a8f280cfc75b42639d051669daf9b35c
Source note	uspto-grants-2014_12