1,2-Dimethylimidazole → 5-(1,2-Dimethyl-1H-imidazol-5-yl)-3-methoxypyridin-2-amine

HRID 523099Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([O:9][CH3:10])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH3:17].CC([O-])=O.[K+]>CC(N(C)C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:11][N:12]1[C:16]([C:2]2[CH:3]=[C:4]([O:9][CH3:10])[C:5]([NH2:8])=[N:6][CH:7]=2)=[CH:15][N:14]=[C:13]1[CH3:17]

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 5-bromo-3-methoxypyridin-2-amine (55.5 mg, 0.273 mmol), 1,2-dimethyl-1H-imidazole (52.6 mg, 0.547 mmol), Pd(OAc)2 (2.5 mg, 0.011 mmol), KOAc (53.7 mg, 0.55 mmol) in DMA (3 mL) was stirred at 150° C. under microwave irradiation for 8 hours. The reaction mixture was filtered, diluted with NaCl solution and extracted with EtOAc. The organic layer was purified by eluting through an SCX-2 column using 2M NH3/MeOH followed by Biotage silica gel column chromatography eluting with 0-12% MeOH/EtOAc to give the title compound as yellow waxy solid (9 mg, 15%).

Workup

filtrationThe reaction mixture was filtered
additiondiluted with NaCl solution
extractionextracted with EtOAc
customThe organic layer was purified
washby eluting through an SCX-2 column
washeluting with 0-12% MeOH/EtOAc

Sources & evidence

ORD record: ord-283dc8291cf74fce95b1dee2030aa040
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334286B2

Reaction notes

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