HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-bromobutanimide → 2-Bromo-1-(2-cyclopropylmethoxypyrimidin-5-yl)ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | 2-Cyclopropylmethoxy-5-(1-ethoxyvinyl)pyrimidine | HCID 118199853 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Oxolane--water (1/1) | HCID 21881883 | — |
| Product | 2-Bromo-1-(2-cyclopropylmethoxypyrimidin-5-yl)ethanone | HCID 118199852 | 71.7% |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
A solution of 480 mg (2.18 mmol) of 2-cyclopropylmethoxy-5-(1-ethoxyvinyl)pyrimidine in 8 mL of a THF/H2O mixture: (6/2: v/v) is cooled to 0° C. under argon. After addition of 380.02 mg (2.11 mmol) of N-bromosuccinimide, the reaction mixture is maintained at 0° C. for 1 hour. The solution obtained is taken up in ethyl acetate and washed with aqueous NaHCO3 solution and then with saturated NaCl solution. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 80/20 DCM/MeOH) to give 410 mg of 2-bromo-1-(2-cyclopropylmethoxypyrimidin-5-yl)ethanone, the characteristics of which are as follows:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321790B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-9372a79e407c4764adbbc7f5b1a76598 |
| Source note | uspto-grants-2016_04 |