HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2204785Generated: October 27, 2026
Methane → 3-(1H-benzo[d]imidazol-2-yl)-5-bromopyrazin-2-amine
https://huagongshe.com/reaction/2204785
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methane | HCID 297 | — |
| Reactant | O-Phenylenediamine | HCID 7243 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Diethyl cyanophosphonate | HCID 76257 | — |
| Reactant | 3-Amino-6-bromopyrazine-2-carboxylic acid | HCID 18521600 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-(1H-benzo[d]imidazol-2-yl)-5-bromopyrazin-2-amine | HCID 52937760 | 60.4% |
Reaction Steps
A mixture of 3-amino-6-bromo-pyrazine-2-carboxylic acid (10 g, 45.87 mmol), benzene-1,2-diamine (5.45 g, 50.46 mmol), diethoxyphosphorylformonitrile (8.23 g, 50.46 mmol) and triethylamine (12.79 mL, 91.74 mmol) in DME (30 mL) was heated in the microwave at 170° C. for 40 minutes. The mixture was allowed to cool and water was added. The resultant dark-coloured precipitate was dissolved in EtOAc and stirred with charcoal for 30 minutes. After filtering through celite, the filtrate was concentrated in vacuo to give the product as a yellow solid (8.04 g, 60% Yield). 1H NMR (400 MHz, DMSO) 7.22-7.32 (2H, m), 7.55 (1H, d), 7.75 (1H, d), 7.8 (1h, br s), 8.8 (1H, br s), 13.1 (1H, s); MS (ES+) 291
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09365557B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-2dac0ae162984770b3b49bbdfa31abfe |
|---|
| Source note | uspto-grants-2016_06 |
|---|