Buchwald–Hartwig amination: (R)-2-chloro-6-(2-fluoroethyl)-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepine → (R)-6-(2-fluoroethyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepin-2-amine

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

100 °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.

• N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine37%
• 1-(8-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-2-(pyridin-3-yl)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanone35%
• (R)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepin-2-amine30%
• (S)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine28%
• N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2-(pyridin-3-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine28%
• N-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]pyrimidin-2-amine19%
• 2-(2-(1,3-Dimethyl-1H-pyrazol-5-yl)-8-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile17%
• 1-(2-(Isopropoxymethyl)-8-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanone15%
• (R)-2-(8-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile8%
• 2-(Isopropoxymethyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine5%
• 2-cyclopropyl-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine0%
• (R)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepin-2-amine15%

Copied from the source record, unedited

3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.118 g, 0.49 mmol), Palladium(II) acetate (9.19 mg, 0.04 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.014 g, 0.04 mmol) and Cesium carbonate (0.00 µmol) were put in a 5 mL microwave vial and sealed and purged with argon. (R)-2-chloro-6-(2-fluoroethyl)-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepine (0.126 g, 0.41 mmol) in DME (5 mL) was added. The reaction mixture was run in the microwave at 100°C for 60 minutes. Reaction still not complete. Additional palladium(II)acetate and 2-(dicyclohexylphosphino)biphenyl (small spatula) and the reaction was run again in the microwave for 60 minutes. The reaction mixture was filtrated through celite, concentrated and purified by preparative chromatography. The productcontaining fractions were po

This record comes from experimental reaction archive (ord-5b8b8e8b9f444b0ba792e38397226bc2). Open the source and check it against what is on this page.

• experimental reaction archive record ord-5b8b8e8b9f444b0ba792e38397226bc2 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.