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

HRID 2178011

Reaction equation

HRID 2178011 reaction equation
[CH:1]1([C:6](=O)[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]=1[OH:26])[CH:21]=O)[CH3:16].[NH2:30][C:31]([NH2:33])=[O:32].Cl>C(O)C>[CH:1]1([C:6]2[NH:33][C:31](=[O:32])[NH:30][CH:21]([C:20]3[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]([OH:26])=[C:18]([O:17][CH2:15][CH3:16])[CH:19]=3)[C:7]=2[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 103976021-Cyclopentyl-2-phenylethan-1-one2×

Product 1

HCID 513471876-cyclopentyl-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-oneYield 3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-cyclopentyl-2-phenylethanone (Intermediate 91) (1.6 mmol, 300 mg), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (1.91 mmol, 404 mg), and urea (4.8 mmol, 288 mg) in anhydrous ethanol (5 mL) was added concentrated HCl (0.2 mL), the above mixture was refluxed for 13 hours. The reaction mixture was concentrated and the residue was purified by column chromatography, followed by preparative HPLC to afford the product Compound 172 as yellow solid (20 mg, yield: 2.96%). 1H NMR (DMSO 400 MHz): δ 10.23 (s, 1H), 8.25 (s, 1H), 6.98-7.33 (m, 8H), 5.00 (d, J=2.4 Hz, 1H), 3.94-4.04 (m, 2H), 2.65-2.69 (t, J=9.2 Hz, 1H), 1.24-1.79 (m, 11H); MS (ESI): m/z 424.1 [M+1]+.

Workup

  1. temperaturethe above mixture was refluxed for 13 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-359d41d7841d49bd83851e81b2460056
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Linked notes

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