N-Cyclopropyl-N'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → (S)-1-cyclopropyl-3-(4-(2-(3-methylmorpholino)pyrimidin-4-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-(4-chloropyrimidin-2-yl)-3-methylmorpholine	HCID 87379247	—
Product	(S)-1-cyclopropyl-3-(4-(2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)urea	HCID 53380860	66%

Reaction Steps

Method as described for intermediate 5 using (S)-4-(4-chloropyrimidin-2-yl)-3-methylmorpholine (intermediate 15) and 4-(3-cyclopropylureido)phenyl boronic acid pinacol ester. Material was purified using flash chromatography (20-90% EtOAc in petroleum ether 40-60) to afford a light pink solid (130 mg, 66%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09249129B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-892f495c659f410e96e7f207009928b4
Source note	uspto-grants-2016_02