Water → 5-(3-(Tetrahydro-2H-pyran-2-yloxy)-1-propynyl)-2-pyridinylamine

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Water	HCID 962	—
Edukt	Dichloromethane	HCID 6344	—
Edukt	2-Pyridinamine, 5-iodo-	HCID 88579	—
Edukt	Tetrahydro-2-(2-propynyloxy)-2H-pyran	HCID 98609	—
Katalysator	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Katalysator	HCID 178418476	HCID 178418476	—
Lösungsmittel	Diethylamine	HCID 8021	—
Produkt	5-(3-(Tetrahydro-2H-pyran-2-yloxy)-1-propynyl)-2-pyridinylamine	HCID 22397241	50%

Reaktionsschritte

2-(2-Propynyloxy)tetrahydro-2H-pyran (360 mg), 5-iodo-2-pyridinylamine (440 mg), CuI (140 mg) and dichlorobis(triphenylphosphine)palladium (60 mg) are dissolved in diethylamine (10 mL). After the mixture is stirred for 1 h at room temperature, water (40 mL) and CH2Cl2 (80 mL) are added. The organic layer is separated, dried (MgSO4) and concentrated. The resulting residue is purified on a silica gel plate (CH2Cl2/methanol, 9/1) to give 230 mg (50%) of the title compound as an oil which slowly solidifies. MS (ESI+) m/z 233 (M+H)+. 1H NMR (CDCl3) δ 8.10, 7.60, 6.65, 5.90, 4.86, 4.48, 3.90, 3.5-3.6, 1.55-1.9.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US06559145B2
Quelldatensatz	uspto-grants-2003_05
ORD ID	ord-dbf94253ffb1440d9bb7917fd401397f
Quellennotiz	uspto-grants-2003_05