HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → (2R)-4-{4-[2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-morpholin-4-yl-9H-purin-8-yl]piperazin-1-yl}-4-oxobutan-2-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 3-Hydroxybutanoic acid, (R)- | HCID 92135 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 5-(9-Isobutyl-6-morpholino-8-(piperazin-1-yl)-9H-purin-2-yl)pyrimidin-2-amine | HCID 59333501 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (2R)-4-{4-[2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-morpholin-4-yl-9H-purin-8-yl]piperazin-1-yl}-4-oxobutan-2-ol | HCID 45376241 | 36% |
Reaction Steps
5-(9-Isobutyl-6-morpholin-4-yl-8-piperazin-1-yl-9H-purin-2-yl)pyrimidin-2-amine (150 mg, 0.33 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (128 mg, 0.67 mmol), 1-hydroxybenzotriazole (45 mg, 0.33 mmol), and (R)-3-hydroxybutyric acid (70 mg, 0.67 mmol) were dissolved in dimethylformamide (5 ml) and the resulting mixture was stirred for 16 hours. The solvent was evaporated under reduced pressure and then the residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid) to give the title compound (62 mg, 36%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08309546B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-3d96df65245543f9b0eec94795cbd73b |
| Source note | uspto-grants-2012_11 |