Hydrochloric Acid → 6-(4-aminophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-one

HRID 2177940Notes

Reaction equation

HRID 2177940 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]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1176UreaHCID 2383351-Phenyl-2-(pyridin-3-yl)ethanone2×HCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehyde

Product 1

HCID 513483616-(4-aminophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-oneYield 43.7%

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

  1. temperatureAfter being cooled down to room temperature
  2. customthe reaction mixture was evaporated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6cf1f673e69e4538b1fc318ac0338910
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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