Sodium Cyanide → 5-Cyano-2,6-Diamino-3-(2,3,5-trichlorophenyl)pyrazine

HRID 1633474Notes

Reaction equation

[C-]#N.[Na+].[Cu][C:5]#[N:6].Br[C:8]1[N:9]=[C:10]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[C:17]=2[Cl:24])[C:11]([NH2:15])=[N:12][C:13]=1[NH2:14]>CN(C)C=O>[C:5]([C:8]1[N:9]=[C:10]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[C:17]=2[Cl:24])[C:11]([NH2:15])=[N:12][C:13]=1[NH2:14])#[N:6]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 97% sodium cyanide (0.064 g, 1.306×10−3 mole) and 90% copper(I) cyanide (0.135 g, 1.306×10−3 mole) in dry dimethylformamide (5 ml) was stirred and heated to 130° C. To the resulting clear solution was added 5-Bromo-2,6-Diamino-3-(2,3,5-trichlorophenyl)pyrazine (0.35 g, 0.95×10−3 mole) in small portions, and the solution was maintained at 140-150° C. for 16 hrs. The reaction mixture was cooled and evaporated in vacuo. The residue was extracted with ethyl acetate (100 ml), washed with water (100 ml) and brine (100 ml), dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated in vacuo. The residue was purified by ‘flash chromatography’ using 5-17% ethyl acetate in cyclohexane as the eluent. Yield 0.152 g (51 %), M.p. 277-279° C.

Workup

temperaturethe solution was maintained at 140-150° C. for 16 hrs
temperatureThe reaction mixture was cooled
customevaporated in vacuo
extractionThe residue was extracted with ethyl acetate (100 ml)
washwashed with water (100 ml) and brine (100 ml)
dry with materialdried over anhydrous magnesium sulphate
filtrationfiltered
customthe filtrate evaporated in vacuo
customThe residue was purified by ‘flash chromatography’

Sources & evidence

ORD record: ord-ac0b28ccb91e4d7698c5b3d772113967
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503909B1

Reaction notes

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