HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 89812826, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-(Cyclopropylmethyl)piperazine | HCID 965875 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 5-Bromopyrimidine-2-carboxylic acid | HCID 16462970 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 89812826 | HCID 89812826 | 29% |
Reaction Steps
To 5-bromopyrimidine-2-carboxylic acid (100 mg, 0.49 mmol) and TBTU (158 mg, 0.49 mmol) in anhydrous DMF 94.4. mL) was added DIPEA (0.36M in CH2Cl2, 1.4 mL, 0.49 mmol) and the reaction mixture stirred at RT for 40 min. N-cyclopropylmethylpiperazine (83 mg, 0.59 mmol) in anhydrous DMF (1 mL) was added and the reaction stirred at RT for 18 h. The reaction mixture was passed through a Si—NH2 cartridge (5 g), eluting with DMF and MeOH. The eluents were combined, concentrated in vacuo and purified by reverse phase preparative HPLC-MS to obtain (5-bromo-pyrimidin-2-yl)-(4-cyclopropylmethyl-piperazin-1-yl)-methanone as a pale yellow solid (46 mg, 29%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09193689B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-5e3ef2d228734defbfa9e748caec6d05 |
| Source note | uspto-grants-2015_11 |