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), 2-(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	US08912205B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-7954e2d783b34bf2ad18d6cdf64d3868
Source note	uspto-grants-2014_12