5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amine → (S)-ethyl-2-(5-(3-ethylureido)pyrazin-2-yl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amine	HCID 17998987	—
Reactant	(S)-tert-butyl 2-(4-(3-ethylureido)phenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate	HCID 59239149	—
Reactant	HCID 86663155	HCID 86663155	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	(S)-ethyl-2-(5-(3-ethylureido)pyrazin-2-yl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate	HCID 66679218	58%

Reaction Steps

Method as described for intermediate 5 using (S)-ethyl 2-chloro-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (intermediate 11), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amine as starting materials, and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) as catalyst. The reaction mixture was filtered through a celite 545 pre-packed cartridge (2.5 g), washed with MeOH and solvent removed in vacuo. The residue was purified by flash chromatography using a gradient of 0-40% DCM/MeOH yielding the title compound (69 mg, 0.18 mmol, 58%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08785457B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-156a9b3514284112882eed945b5c0dd5
Source note	uspto-grants-2014_07