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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

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethaneHCID 297—
ReactantO-PhenylenediamineHCID 7243—
ReactantTriethylamineHCID 8471—
ReactantDiethyl cyanophosphonateHCID 76257—
Reactant3-Amino-6-bromopyrazine-2-carboxylic acidHCID 18521600—
SolventWaterHCID 962—
Solvent1,2-DimethoxyethaneHCID 8071—
SolventEthyl AcetateHCID 8857—
Product3-(1H-benzo[d]imidazol-2-yl)-5-bromopyrazin-2-amineHCID 5293776060.4%

Reaction Conditions

Temperature170 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365557B2
Source datasetuspto-grants-2016_06
ORD IDord-2dac0ae162984770b3b49bbdfa31abfe
Source noteuspto-grants-2016_06