HuagongsheHuagongshe Chemistry Print Report · For research reference only
1H-Benzimidazol-4-ylboronic acid → 2-(1H-benzo[d]imidazol-4-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1H-Benzimidazol-4-ylboronic acid | HCID 45077856 | — |
| Reactant | HCID 86670087 | HCID 86670087 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | 2-(1H-benzo[d]imidazol-4-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine | HCID 60197767 | — |
Reaction Steps
The title compound was prepared in a manner similar to EXAMPLE 1 using 2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 50 mg, 0.221 mmol), 1H-benzo[d]imidazol-4-ylboronic acid (71.5 mg, 0.441 mmol) and PdCl2(dppf) (12.91 mg, 0.018 mmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.03 (dd, J=11.87, 8.59 Hz, 1 H), 3.33-3.75 (m, 5 H), 3.98 (m, 2 H), 4.74-4.84 (m, 1 H), 6.49-7.07 (br s, 1 H), 7.54 (t, J=7.83 Hz, 1 H), 7.79-7.91 (m, 2 H), 8.25-8.33 (m, 1 H), 8.98 (s, 1 H), 12.18-12.29 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C16H16N6O, 309.14; found 309.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09045496B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-f08e3d28987a4ea5a9b8cd33a7ca60eb |
| Source note | uspto-grants-2015_06 |