4-Pyridinemethanamine → [7-(3,4-Dimethoxy-phenyl)-imidazo[1,2-c]pyrimidin-5-yl]pyridin-4-ylmethyl-amine
Reaction equation
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[N:3]=1.[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.C(N(C(C)C)CC)(C)C>CC(O)C>[CH3:20][O:19][C:13]1[CH:12]=[C:11]([C:4]2[N:3]=[C:2]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[N:7]3[CH:8]=[CH:9][N:10]=[C:6]3[CH:5]=2)[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
The mixture of 5-chloro-7-(3,4-dimethoxyphenyl)-imidazo[1,2-c]pyrimidine (57.94 mg, 0.2 mmol), 4-aminomethylpyridine (23.79 mg, 0.22 mmol), and diisopropylethylamine (38.78, 0.3 mmol) in 2-propanol was stirred at 90° C. for 20 h, and cooled to room temperature. The solvent was evaporated, and 5 ml of ice water was added. Then the resulting product was extracted with 2×10 ml of ethyl acetate. The combined extract was dried over MgSO4. Then the solvent was evaporated and 2 ml of ether was added. The produced solid was collected by filtration and dried to give pure product (38 mg, 52.6%) of [7-(3,4-dimethoxy-phenyl)-imidazo[1,2-c]pyrimidin-5-yl]pyridin-4-ylmethyl-amine.
Workup
- temperaturecooled to room temperature
- customThe solvent was evaporated
- addition5 ml of ice water was added
- extractionThen the resulting product was extracted with 2×10 ml of ethyl acetate
- extractionThe combined extract
- dry with materialwas dried over MgSO4
- customThen the solvent was evaporated
- addition2 ml of ether was added
- filtrationThe produced solid was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-5ace11e4df714cb885be6f4f3d0af7a1
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06911443B2
Reaction notes
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