HuagongsheHuagongshe Chemistry Print Report · For research reference only
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 | US06723726B1 |
| Source dataset | uspto-grants-2004_04 |
| ORD ID | ord-86122228fecf44cdb2e615af0fe37903 |
| Source note | uspto-grants-2004_04 |