Hydrochloric Acid → 6-(4-aminophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-one
Reaction equation
[C:1]1([C:7](=O)[CH2:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]=1[OH:27])[CH:22]=O)[CH3:17].[NH2:31][C:32]([NH2:34])=[O:33].Cl.[CH2:36](O)C>>[NH2:11][C:12]1[CH:36]=[CH:10][C:9]([C:8]2[NH:34][C:32](=[O:33])[NH:31][CH:22]([C:21]3[CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]([OH:27])=[C:19]([O:18][CH2:16][CH3:17])[CH:20]=3)[C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][CH:13]=1Participants
6
Conditions
- Temperature
- 78 °C
Procedure
A mixture of 1-phenyl-2-(pyridin-3-yl)ethanone (Intermediate 42) (200 mg, 1.01 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (213.3 mg, 1.01 mmol), urea (181.8 mg, 3.03 mmol), and concentrated hydrochloric acid solution (0.5 mL) in ethanol (2 mL) was refluxed at 78° C. for 70 h. After being cooled down to room temperature, the reaction mixture was evaporated, and the residue was purified by preparative HPLC to give Compound 84 (191.1 mg, yield 43.7%). 1H NMR (DMSO-d6 400 MHz): δ 10.34 (s, 1H), 9.06 (s, 1H), 8.35-8.33 (m, 1H), 8.10 (d, J=2.0 Hz, 1H), 7.72 (s, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.45-7.39 (m, 2H), 7.33-7.23 (m, 6H), 5.39 (d, J=2.8 Hz, 1H), 4.11-4.06 (m, 2H), 1.36-1.33 (m, 3H); MS (ESI): m/z 433.0 [M+H]+.
Workup
- temperatureAfter being cooled down to room temperature
- customthe reaction mixture was evaporated
- customthe residue was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-ba77091422aa4681ab67ce3ea5e62024
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08741915B2
Reaction notes
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