HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 6-(Bromomethyl)thieno[3,2-b]pyrazine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Phosphorus tribromide | HCID 24614 | — |
| Reactant | Thieno[2,3-b]pyrazin-6-ylmethanol | HCID 67125540 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 6-(Bromomethyl)thieno[3,2-b]pyrazine | HCID 67125550 | 63.3% |
Reaction Steps
To a suspension of thieno[3,2-b]pyrazin-6-ylmethanol 87 (408 mg, 2.455 mmol) in CH2Cl2 (8 mL) and THF (8 mL) was added phosphorus tribromide (1/166 mL, 12.27 mmol) and stirred overnight at rt. Water was added, alkalized with 2N NaOH and extracted with EtOAc. Organic layer was washed with NaHCO3 (aq) solution, brine, dried and evaporated. Purification by chromatography (CH2CL2) gave pure 6-(bromomethyl)thieno[3,2-b]pyrazine 47 (356 mg, 63%). NMR (400 MHz, CDCl3) 4.80 (s, 2H), 7.71 (s, 1H), 8.49 (d, J=2.3 Hz, 1H), 8.64 (d, J=2.3 Hz, 1H). (m/z)=229 and 231 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08669256B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-41b48f1c844b4fc88f92fdcaca56d5da |
| Source note | uspto-grants-2014_03 |