Ammonium Chloride → 1,1-dimethylethyl 4-(6-((9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-5-methyl-3-pyridinyl)-1-piperazinecarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Ammonium Chloride	HCID 25517	—
Reactant	tert-Butyl piperazine-1-carboxylate	HCID 143452	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	N-(5-bromo-3-methyl-2-pyridinyl)-9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine	HCID 58299572	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	1,1-dimethylethyl 4-(6-((9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-5-methyl-3-pyridinyl)-1-piperazinecarboxylate	HCID 58299634	53.4%

Reaction Conditions

Temperature	140 °C

Reaction Steps

Sodium 2-methylpropan-2-olate (0.100 g, 1.06 mmol) was combined with compound 77 (0.150 g, 0.354 mmol) and tert-butyl 1-piperazinecarboxylate (0.099 g, 0.532 mmol) in 1,4-dioxane (3 ml). Nitrogen was bubbled through the solution for 1 min before adding XANTPHOS (0.031 g, 0.053 mmol) and Pd2(dba)3 (0.024 g, 0.026 mmol). The reaction mixture was heated to 140° C. using microwave irradiation for 1 hour. The reaction mixture was poured into sat. NH4Cl, and extracted with 10% isopropanol/DCM. The organic layer was dried over MgSO4 and concentrated in vacuum. The crude product was purified by flash column chromatography, eluting with a gradient of DCM-7% methanol/DCM to provide compound 78 as a brown oil (100 mg). LCMS-ESI (POS), M/Z, M+1: Found 529.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08980903B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-204abdc919274010a662c625e759cb15
Source note	uspto-grants-2015_03