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

HRID 401076Notes

Reaction equation

HRID 401076 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([S:13][CH3:14])[C:11]=1[OH:12])[CH:7]=O)[CH3:2].[C:15]1([C:21](=O)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH2:30][C:31]([NH2:33])=[O:32].Cl>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:7]2[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:33][C:31](=[O:32])[NH:30]2)[CH:9]=[C:10]([S:13][CH3:14])[C:11]=1[OH:12])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 86669336HCID 86669336, compound2×

Product 1

HCID 670611304-(3-ethoxy-4-hydroxy-5-(methylthio)phenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-oneYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-ethoxy-4-hydroxy-5-(methylthio)benzaldehyde (Intermediate 50) (300 mg, 1.42 mmol), 1,2-diphenylethanone (330 mg, 1.68 mmol) and urea (170 mg, 2.80 mmol) in ethanol (5 mL) was added conc. HCl (0.3 mL) and the reaction mixture was refluxed under N2 atmosphere overnight. The resulting mixture was cooled and purified by silica gel column to give desired product (200 mg, yield 33%).

Workup

  1. temperaturethe reaction mixture was refluxed under N2 atmosphere overnight
  2. temperatureThe resulting mixture was cooled
  3. custompurified by silica gel column

Sources & evidence

ORD record
ord-6c50e8d7c8fc4398b54701a7a31e8bdc
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

Loading…