Hydrochloric Acid → 4-(3-bromo-5-ethoxy-4-hydroxyphenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one

HRID 2177955Notes

Reaction equation

HRID 2177955 reaction equation
[C:1]1([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([O:26][CH2:27][CH3:28])[C:24]=1[OH:25])[CH:20]=O.[NH2:29][C:30]([NH2:32])=[O:31].Cl>CCO>[Br:16][C:17]1[CH:18]=[C:19]([CH:20]2[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[NH:32][C:30](=[O:31])[NH:29]2)[CH:22]=[C:23]([O:26][CH2:27][CH3:28])[C:24]=1[OH:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehyde

Product 1

HCID 569614644-(3-bromo-5-ethoxy-4-hydroxyphenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-oneYield 11.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1,2-diphenylethanone (4.80 g, 25 mmol), 3-bromo-5-ethoxy-4-hydroxybenzaldehyde (5.00 g, 20 mmol) and urea (3.68 g, 61 mmol) in EtOH (250 mL) was added conc. HCl (10 mL). The mixture was heated at reflux for 112 h. Followed standard aqueous workup procedure and purified by silica gel column chromatography (PE:EA=1:3) to afford Compound 100 as a white solid (1.06 g, 11%). 1H NMR (MeOH-d4 500 MHz TMS): δ 7.24 (s, 5H), 7.09 (s, 1H), 7.04 (s, 3H), 6.85 (s, 3H), 5.17 (s, 1H), 4.03 (m, 2H), 1.37 (t, J=7.5 Hz, 3H); MS (ESI): m/z 465.0 [M+1]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 112 h
  3. customFollowed standard aqueous workup procedure and purified by silica gel column chromatography (PE:EA=1:3)

Sources & evidence

ORD record
ord-42522f4553014ebe87fc3ae41d636d3a
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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