Methanol → Ethyl 1-(5-(7-bromo-2-(3-ethylureido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	1-(7-Bromo-5-iodobenzo[d]thiazol-2-yl)-3-ethylurea	HCID 57813723	—
Reactant	Ethyl 4-methyl-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)piperidine-4-carboxylate	HCID 66976878	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Ethyl 1-(5-(7-bromo-2-(3-ethylureido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate	HCID 86663956	41.2%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a solution of Intermediate 3 (22.7 g, 53.2 mmol) and iv (20 g, 53.2 mmol) in 1,4-dioxane:MeOH (300:180 mL) was added potassium phosphate (17 g, 79 mmol) at RT. The resulting mixture was degassed for 15-20 min by purging N2 followed by the addition of Pd(PPh3)4 (6.1 g, 5.32 mmol). The reaction mixture was again degassed for another 15-20 min and then heated up to 80° C. for 5 h. The reaction mixture was cooled to RT, diluted with EtOAc (500 mL) and passed through celite bed. The filtrate was evaporated and the crude residue was purified by chromatography on silica eluting with 1.5% MeOH:DCM to obtain Intermediate 7 (12 g, 41%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08906902B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-3e31e0b914d043148a4dd686dc4dc55a
Source note	uspto-grants-2014_12