1-Cyclopropyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → (S)-1-cyclopropyl-3-(3-fluoro-4-(4-(5-fluoropyridin-3-yl)-6-(3-methylmorpholino)pyrimidin-2-yl)phenyl)urea

Participants

Role	Name	HCID	Charge
Reactant	1-Cyclopropyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea	HCID 66679229	—
Reactant	(S)-4-(6-(5-fluoropyridin-3-yl)-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholine	HCID 67382782	—
Reactant	(S)-4-(2-chloro-6-(5-fluoropyridin-3-yl)pyrimidin-4-yl)-3-methylmorpholine	HCID 86691143	—
Product	(S)-1-cyclopropyl-3-(3-fluoro-4-(4-(5-fluoropyridin-3-yl)-6-(3-methylmorpholino)pyrimidin-2-yl)phenyl)urea	HCID 53379769	—

Reaction Steps

Method as described for intermediate 5 using (S)-4-(2-chloro-6-(5-fluoropyridin-3-yl)pyrimidin-4-yl)-3-methylmorpholine (intermediate 7) and 1-cyclopropyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (intermediate 11). Material was purified by prep HPLC twice (low pH) followed by purification using a TsOH cartridge (100 mg) to afford a yellow solid, (4.5 mg, 15%)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09249129B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-4e3fdfd620f8482696571ef061d9a010
Source note	uspto-grants-2016_02