1,4-Dioxane → (1-Benzyl-1H-indazol-5-yl)-(6-(5-[1,3-dioxolan-2-yl]-furan-2-yl)-pyrido[3,4-d]pyrimidin-4-yl)-amine

Participants

Role	Name	HCID	Charge
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	(1-Benzyl-1H-indazol-5-yl)-(6-chloropyrido[3,4-d]pyrimidin-4-yl)-amine	HCID 21952012	—
Reactant	2-(Tributylstannyl)-5-(1,3-dioxolan-2-ylmethyl)-furan	HCID 22727416	—
Catalyst	(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)	HCID 10974057	—
Product	(1-Benzyl-1H-indazol-5-yl)-(6-(5-[1,3-dioxolan-2-yl]-furan-2-yl)-pyrido[3,4-d]pyrimidin-4-yl)-amine	HCID 21951893	—

Reaction Steps

(1-Benzyl-1H-indazol-5-yl)-(6-chloro-pyrido[3,4-d]pyrimidin-4-yl)-amine (4.28 g), 2-(tributylstannyl)-5-(1,3-dioxolan-2-ylmethyl)-furan (J. Chem Soc., Chem. commun., (1988), p560) (10 g) and 1,4-bis(diphenylphosphino)butane palladium (II) chloride (1 g) were heated at reflux in dioxane (150 ml) for 24 hr (Procedure B). The solvent was removed in vacuo and the residue chromatographed on silica. Subsequent trituration gave the title compound as a yellow solid: δH [2H6]-DMSO 10.46 (1H,s), 9.17 (1H,s), 8.74 (1H,s), 8.52 (1H,s), 8.23 (1H,s), 8.18 (1H,s), 7.80-7.68 (2H,m), 7.41-7.22 (5H,m), 7.17 (1H,d), 6.80 (1H,d), 6.06 (1H,s), 5.71 (2H,s), 4.20-3.96 (4H,m).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06174889B1
Source dataset	uspto-grants-2001_01
ORD ID	ord-3be8eb624114482c9c5768dbef392f0c
Source note	uspto-grants-2001_01