Potassium Carbonate → (S)-tert-butyl (1-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-5-(3-carbamoyl-4-fluorophenyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(3-Carbamoyl-4-fluorophenyl)boronic acid	HCID 44717530	—
Reactant	(S)-tert-butyl (1-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-5-bromopyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate	HCID 90290212	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	toluene IPA water	HCID 66631872	—
Product	(S)-tert-butyl (1-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-5-(3-carbamoyl-4-fluorophenyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate	HCID 90290213	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

In a microwave tube were charged with compound 23C (52 mg, 0.1 mmol), (3-carbamoyl-4-fluorophenyl)boronic acid (27 mg, 0.15 mmol), K2CO3 (41 mg, 0.3 mmol), Pd(dppf)Cl2 (5 mg). To the mixture was added 2 mL of Toluene/2-propanol/H2O (3/1/1). The mixture was heated up to 120° C. for 20 min in a Microwave Synthesizer. The mixture was partitioned between ethyl acetate and water. The organic layer was separated and concentrated to afford crude product used for next step without further purification. MS (m/z) 582.73 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09050344B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-aeea0dfc57894ec59b56e49d4d221f2f
Source note	uspto-grants-2015_06