Potassium Carbonate → HCID 73555062, compound

HRID 1396456Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])[CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+].C([O-])([O-])=O.[K+].[K+].C[N:22](C)CCN>[Cu-]=O.C(O)CO>[NH2:22][C:2]1[N:7]=[C:6]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A heavy walled resealable tube was loaded, under an argon atmosphere, with copper (I) oxide (159 mg, 1.11 mmol), 2-(6-bromopyridin-2-yl)-2-methylpropanenitrile (5000 mg, 22.2 mmol), ammonium hydroxide 28% solution (26.9 mL, 444 mmol), K2CO3 (614 mg, 4.44 mmol), N,N-dimethylethylenediamine (196 mg, 244 μA, 2.22 mmol) and ethyleneglycol (44.4 mL). The reaction was heated to 60° C. with stirring for 6 h. After cooling down, the reaction mixture was extracted with dichloromethane (3×25 mL), combined organics dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (silica gel 50 μm, 40 g, Analogix) eluting with 0 to 5% over 20 min (10% ammonium hydroxide in methanol)/dichloromethane, obtained 2-(6-aminopyridin-2-yl)-2-methylpropanenitrile (3.2 g, 89.4% yield) as a white solid. 1H NMR (CHLOROFORM-d) δ: 7.34-7.46 (m, 1H), 6.81 (d, J=7.2 Hz, 1H), 6.40 (d, J=7.9 Hz, 1H), 4.67 (br. s., 2H), 1.63-1.68 (m, 6H); LC-MS 162.1 [M+H]+.

Workup

temperatureAfter cooling down
extractionthe reaction mixture was extracted with dichloromethane (3×25 mL)
dry with materialcombined organics dried over magnesium sulfate
customevaporated
customThe residue was purified by flash chromatography (silica gel 50 μm, 40 g, Analogix)
washeluting with 0 to 5% over 20 min (10% ammonium hydroxide in methanol)/dichloromethane

Sources & evidence

ORD record: ord-01212ba5478a4fbdb901a80dbd3be196
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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