2-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → (S)-ethyl 2-(4-amino-3-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	2-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline	HCID 17906172	—
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	—
Product	(S)-ethyl 2-(4-amino-3-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate	HCID 66679065	88%

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) and 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline as starting materials. The reaction mixture was filtered through a celite 545 pre-packed cartridge (2.5 g), washed with MeOH and reduced in vacuo. The residue was purified by flash SCX2 chromatography affording the title compound (130 mg, 0.32 mmol, 88%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08785457B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-3b2b4e2f5d8e40a9a54a38c3d05e57f6
Source note	uspto-grants-2014_07