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

HRID 2267400
Notes
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Reaction equation

HRID 2267400 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-9435be50b2b54763bf5effd79a3f5d96
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858785B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes