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

Participants

Role	Name	HCID	Charge
Reactant	N-Cyclopropyl-N'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea	HCID 44119149	—
Reactant	(S)-4-(6-(5-fluoropyridin-3-yl)-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholine	HCID 67382782	—
Reactant	(S)-4-(2-chloro-6-(pyridin-2-yl)pyrimidin-4-yl)-3-methylmorpholine	HCID 86691152	—
Product	(S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6-(pyridin-2-yl)pyrimidin-2-yl)phenyl)urea	HCID 53379442	—

Reaction Steps

Method as described for intermediate 5 using (S)-4-(2-chloro-6-(pyridin-2-yl)pyrimidin-4-yl)-3-methylmorpholine (intermediate 21) and 4-(3-cyclopropylureido)phenyl boronic acid pinacol ester. Material was purified by prep HPLC (low pH) to afford a light orange solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09249129B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-275ab3f445cf47eab959890850454bb7
Source note	uspto-grants-2016_02