Sodium Cyanide → HCID 16070452, compound

HRID 1710712Notes

Reaction equation

[C-]#N.[Na+].[Cu][C:5]#[N:6].Br[C:8]1[C:9]([NH2:25])=[N:10][C:11]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)=[C:12]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[N:13]=1>CN(C)C=O>[NH2:25][C:9]1[C:8]([C:5]#[N:6])=[N:13][C:12]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:11]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)[N:10]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of sodium cyanide (21 mg, 0.42 mmol) and copper (I) cyanide (38 mg, 0.42 mmol) in anhydrous dimethylformamide (1.5 mL) was heated to 120° C. 3-Bromo-6-(2-furyl)-5-pyridin-4-ylpyrazin-2-amine (Example 62, 90 mg, 0.28 mmol) was added in portions. After stirring at 120° C. for two hours, the mixture was cooled and evaporated. A 0.75M aqueous solution of sodium cyanide (6 mL) was added, stirred for 10 min at room temperature and partitioned between water and ethyl acetate. The aqueous phase was extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4), and evaporated. Silica gel flash column chromatography (dichloromethane/methanol 98:2) furnished the title compound as a dark yellow solid (52 mg, 70%).

Workup

temperaturethe mixture was cooled
customevaporated
additionA 0.75M aqueous solution of sodium cyanide (6 mL) was added
stirringstirred for 10 min at room temperature
custompartitioned between water and ethyl acetate
extractionThe aqueous phase was extracted twice with ethyl acetate
washthe organic layers washed with brine
dry with materialdried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-6085cc1332994685be1699f8c755a592
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790728B2

Reaction notes

Loading…