Water → 2-Ethyl-4-pyrimidinamine

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Triethylborane	HCID 7357	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	2-Chloro-4-aminopyrimidine	HCID 345752	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-Ethyl-4-pyrimidinamine	HCID 13925296	24.4%

Reaction Steps

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 2-chloropyrimidin-4-amine (2.60 g, 20.0 mmol), triethylborane (20.0 mL, 1.0 M in THF, 20.0 mmol), Pd(dppf)Cl2 (816 mg, 1.0 mmol), K3PO4 (13.0 g, 40.0 mmol), water (2 mL), and tetrahydrofuran (50 mL). After three cycles of vacuum/argon flush, the mixture was heated at reflux for 14 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with 40:1 dichloromethane/methanol to afford 229a as yellow solid (600 mg, 24%). MS-ESI: [M+H]+ 124.3

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09238655B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-bc12d6b4019e45538053503a395015a9
Source note	uspto-grants-2016_01