Triethylamine → Tert-butyl 4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoate
Reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:20]=[CH:19][C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:10][CH:9]=2)=[CH:4][N:3]=1.Cl[CH:22]([C:25]1([C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[N:34]=[CH:33][CH:32]=[CH:31]3)[CH2:27][CH2:26]1)[CH:23]=O.C(N(CC)CC)C>C(O)(C)C>[N:34]1[C:35]2[C:30](=[CH:29][C:28]([C:25]3([C:22]4[N:3]5[CH:4]=[C:5]([C:8]6[CH:9]=[CH:10][C:11]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[CH:19][CH:20]=6)[CH:6]=[N:7][C:2]5=[N:1][CH:23]=4)[CH2:27][CH2:26]3)=[CH:37][CH:36]=2)[CH:31]=[CH:32][CH:33]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of tert-butyl 4-(2-aminopyrimidin-5-yl)benzoate (0.144 g, 0.531 mmol) and chloro(1-quinolin-6-ylcyclopropyl)acetaldehyde (0.156 g, 0.637 mmol) in isopropyl alcohol (3 mL) was heated at 90° C. overnight. The mixture was adjusted to pH=9 using triethylamine, solvent was removed and the residue was purified by chromatography on silica gel using MeOH in methylene chloride (0-5%) to afford the desired product (125 mg, 50.9%). LCMS: (M+H)=463.1.
Workup
- customwas removed
- customthe residue was purified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-681c582e4eda43d38b34e582c63d3e2b
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767675B2
Reaction notes
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