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-fluoro-2-(methylsulfonyl)phenyl)-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-fluoro-2-(methylsulfonyl)phenyl)pyrimidin-4-yl)-3-methylmorpholine	HCID 86691149	—
Product	(S)-1-cyclopropyl-3-(3-fluoro-4-(4-(5-fluoro-2-(methylsulfonyl)phenyl)-6-(3-methylmorpholino)pyrimidin-2-yl)phenyl)urea	HCID 53379772	—

Reaction Steps

Method as described for intermediate 5 using (S)-4-(2-chloro-6-(5-fluoro-2-(methylsulfonyl)phenyl)pyrimidin-4-yl)-3-methylmorpholine (intermediate 10) 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 (low pH) to afford a brown gum, (70 mg, 47%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09249129B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-80298e89975a4419afe26f54c2dc7c03
Source note	uspto-grants-2016_02