Isopropanol → 5,5-Dimethyl-1-(2-((4-(3-phenyl-2-thienyl)-2-pyrimidinyl)amino)ethyl)-2,4-imidazolidinedione

HRID 507624Notes

Reaction equation

HRID 507624 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.Cl.[CH3:20][C:21]1([CH3:34])[N:25]([CH2:26][CH2:27][NH:28][C:29]([NH2:31])=[NH:30])[C:24](=[O:32])[NH:23][C:22]1=[O:33].[OH-].[Na+].CC(O)C>ClCCl.O>[CH3:20][C:21]1([CH3:34])[N:25]([CH2:26][CH2:27][NH:28][C:29]2[N:31]=[C:5]([C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:4]=[CH:3][N:30]=2)[C:24](=[O:32])[NH:23][C:22]1=[O:33]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 684650323-(Dimethylamino)-1-(3-phenylthiophen-2-yl)prop-2-en-1-oneHCID 1784294231-(2-(5,5-Dimethyl-2,4-dioxoimidazolidin-1-yl)ethyl)guanidine hydrochloride

Product 1

HCID 602045225,5-Dimethyl-1-(2-((4-(3-phenyl-2-thienyl)-2-pyrimidinyl)amino)ethyl)-2,4-imidazolidinedioneYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A flask charged with 3-(dimethylamino)-1-(3-phenylthiophen-2-yl)prop-2-en-1-one (52 mg, 0.20 mmol), 1-(2-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)ethyl)guanidine hydrochloride (100 mg, 0.40 mmol) and sodium hydroxide (40 mg, 1.0 mmol) and IPA (3.0 mL) was heated to reflux under nitrogen. After 18 h, the reaction mixture was allowed to cool and then diluted with dichloromethane and water. The organic layer was separated and washed with one portion of water and two portions of brine. The organics were then concentrated and the residue purified by preparative TLC eluted with 3% MeOH/dichloromethane to afford the product (27 mg, 0.066 mmol, 33% yield). MS (M+H)+ 408.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen
  3. temperatureto cool
  4. customThe organic layer was separated
  5. washwashed with one portion of water and two portions of brine
  6. concentrationThe organics were then concentrated
  7. customthe residue purified by preparative TLC
  8. washeluted with 3% MeOH/dichloromethane

Sources & evidence

ORD record
ord-e2ef4eff7167431ea08c9f13aa5cbe08
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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