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), 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	US06713485B2
Source dataset	uspto-grants-2004_03
ORD ID	ord-72d58c0832d7481293fe4e4035a160b0
Source note	uspto-grants-2004_03