Stannane, tributyl[5-(1,3-dioxolan-2-yl)-2-furanyl]- → (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	Stannane, tributyl[5-(1,3-dioxolan-2-yl)-2-furanyl]-	HCID 10960952	—
Reactant	(1-Benzyl-1H-indazol-5-yl)-(6-chloropyrido[3,4-d]pyrimidin-4-yl)-amine	HCID 21952012	—
Catalyst	(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)	HCID 10974057	—
Solvent	1,4-Dioxane	HCID 31275	—
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-chloropyrido[3,4-d]pyrimidin-4-yl)-amine (4.28 g), (tributylstannyl)-5-(1,3-dioxolan-2-yl)-furan (J. Chem Soc., Chem. Commun., (1988), p 560) (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; [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	US08513262B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-6f63546488634667bc1057dfaef42c89
Source note	uspto-grants-2013_08