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

HRID 401006Notes

Reaction equation

HRID 401006 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:20]([O:22][C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([N+:32]([O-:34])=[O:33])[C:30]=1[OH:31])[CH:26]=O)[CH3:21].[NH2:35][C:36]([NH2:38])=[O:37].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:26]([C:25]3[CH:28]=[C:29]([N+:32]([O-:34])=[O:33])[C:30]([OH:31])=[C:23]([O:22][CH2:20][CH3:21])[CH:24]=3)[NH:35][C:36](=[O:37])[NH:38][C:12]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 123366833,4-Dimethoxy-2-phenylacetophenone2×

Product 1

HCID 513477765-(3,4-dimethoxyphenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-3,4-dihydropyrimidin-2(1H)-oneYield 9.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(3,4-dimethoxyphenyl)-1-phenylethanone (Intermediate 7) (130 mg, 0.5 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (106 mg, 0.5 mmol) and urea (69 mg, 1.5 mmol) in 20 mL of ethanol was added 0.2 mL of concentrated HCl, then the mixture was stirred at reflux for 4 days. After the solvent was removed under reduced pressure, the residue was purified by thin layer chromatography (PE:EtOAc=1:2) to give Compound 24 (24.3 mg, yield 9.8%). 1H NMR (CD3OD 400 MHz): δ 7.62 (d, J=1.6 Hz, 1H), 7.30 (s, 5H), 7.17 (s, 1H), 6.68 (d, J=8.0 Hz, 1H), 6.51 (dd, J=2.0 Hz, 8.0 Hz, 1H), 6.38 (d, J=2.0 Hz, 1H), 5.30 (s, 1H), 4.09-4.06 (m, 2H), 3.71 (s, 3H), 3.41 (s, 3H), 1.40 (t, J=7.2 Hz, 3H); MS (ESI): m/z 492.3 [M+1]+.

Workup

  1. temperatureat reflux for 4 days
  2. customAfter the solvent was removed under reduced pressure
  3. customthe residue was purified by thin layer chromatography (PE:EtOAc=1:2)

Sources & evidence

ORD record
ord-f8453efc51b44654b1394f8776c8bfb5
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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