Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Ethyl 2-chloro-4-iodopyridine-3-carboxylate | HCID 15850399 | — |
| Reactant | Ureido-acetic acid tert-butyl ester | HCID 86641479 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 2-Methylpentane | HCID 7892 | — |
| Product | (5-Chloro-2,4-dioxo-1,4-dihydro-2H-pyrido[4,3-d]pyrimidin-3-yl)-acetic acid tert-butyl ester | HCID 86641480 | — |
Reaction Steps
A 2-5 ml microwave vial is charged with Pd(OAc)2 (2.5 mol %, 4.1 mg, 0.016 mmol), Xantphos (5 mol %, 24.9 mg, 0.0321 mmol), ureido-acetic acid tert-butyl ester (190.3 mg, 1.03 mmol), and Cs2CO3 (578.9 mg, 1.605 mmol). 2-Chloro-4-iodo-nicotinic acid ethyl ester (208.9 mg, 0.642 mmol) is added followed by 1,4-dioxane (4 ml). The vessel is sealed and treated in the microwave at 120° C. for 3600 seconds. EtOAc is added to the mixture, washed with brine (3×20 ml), then water (2×20 ml). The organic portions are passed through Celite® and the solvent removed in vacuo. The crude material is taken up in a minimal amount of DCM and loaded onto a 10 g Isolute™ pre packed Silica II cartridge, eluted with 100% iso-hexane to 50% EtOAc:Isohexane to afford the title compound; [M+H]+ 312
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08633211B2 |
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| Source dataset | uspto-grants-2014_01 |
|---|
| ORD ID | ord-c4dcaca36d254cc1be9497421259d9f9 |
|---|
| Source note | uspto-grants-2014_01 |
|---|
