Buchwald–Hartwig amination: 6-Chloropyrazine-2-carbonitrile → Ethyl 2-[(6-cyanopyrazin-2-yl)amino]-1,3-oxazole-5-carboxylate

Drawn from the record's atom map: which bonds break and which form between the reactants and products the source listed. It shows a change in connectivity, not a simulated trajectory and not a mechanism.

Temperature

160 °C

Only the dimensions the source stated are listed. Anything absent here was not recorded, and it is not inferred from what the class usually needs.

No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.

• Ethyl 2-[(5-nitro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate86%
• Ethyl 2-[[6-(trifluoromethyl)-2-pyridinyl]amino]-1,3-oxazole-5-carboxylate68%
• Ethyl 2-[(5-ethoxycarbonyl-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate67%
• Ethyl 2-[[5-(trifluoromethyl)-2-pyridinyl]amino]-1,3-oxazole-5-carboxylate61%
• Ethyl 2-[(4-cyano-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate60%
• Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate48%
• Ethyl 2-(pyridin-2-ylamino)-1,3-oxazole-5-carboxylate38%
• Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate0%
• Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate0%
• Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate0%
• Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate0%

Copied from the source record, unedited

Objective: Test of scope in the coupling of ester substituted aminooxazole To an oven-dried microwave vial was added ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 mmol), 6-chloropyrazine-2-carbonitrile (139 mg, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, 0.02 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.4 mg, 0.075 mmol) and the vial was capped and purged with nitrogen. dioxane (4 mL) (degassed) was added and the reaction mixture was heated to 160 °C for 1 h under microwave irradiation. DCM (20 mL) was added to the crude reaction mixture together with silica (2 g) and the solvent was removed under reduced pressure. The resulting residue was added to a dry-load tube prior to chromatography.The crude pr

This record comes from experimental reaction archive (ord-0b0035404bff4099a5e08c9ac05b0329). Open the source and check it against what is on this page.

• experimental reaction archive record ord-0b0035404bff4099a5e08c9ac05b0329 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.

  experimental record · quality medium · source

experimental reaction record.