4-N-ethylpyridine-3,4-diamine → 3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine
Reaction equation
[NH2:1][C:2]1[C:3]([CH:8]=O)=[N:4][CH:5]=[CH:6][N:7]=1.[CH2:10]([NH:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[NH2:19])[CH3:11].S([O-])(O)=O.[Na+]>CC(N(C)C)=O>[CH2:10]([N:12]1[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N:19]=[C:8]1[C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[CH:5][N:4]=1)[CH3:11]Participants
5
Conditions
- Temperature
- 200 °C
Procedure
3-aminopyrazine-2-carbaldehyde (made in example 1(c)) (0.30 g, 2.4 mmol), N4-ethylpyridine-3,4-diamine (made in example 1(b)) (0.36 g, 2.6 mmol), and sodium hydrogensulfite (0.30 g) were combined in 3 mL of dimethylacetamide and heated to 200° C. in a SmithSynthesizer microwave for 10 minutes. The reaction mixture was partitioned between ethyl acetate and water. The reaction was extracted with ethyl acetate (×3), and the combined organic layers were washed with water and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. After filtration, the organics were concentrated in vacuo. Trituration with diethyl ether affords the title compound as tan solids (0.46 g, 80%).
Workup
- customThe reaction mixture was partitioned between ethyl acetate and water
- extractionThe reaction was extracted with ethyl acetate (×3)
- washthe combined organic layers were washed with water and saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- filtrationAfter filtration
- concentrationthe organics were concentrated in vacuo
Sources & evidence
- ORD record
- ord-96d72e5a63d649f59cc2dbf1ede16ada
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07598251B2
Reaction notes
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