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Potassium Carbonate → 5,7-dimethyl-2-((1-methyl-4-phenyl-1H-imidazol-2-ylthio)methyl)imidazo[1,2-a]pyrimidine

HRID 1094040
Notes
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Reaction equation

HRID 1094040 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[N:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[N:6]2[CH:13]=1.[CH3:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:17][C:16]1=[S:26].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:12][C:7]1[N:6]2[CH:13]=[C:3]([CH2:2][S:26][C:16]3[N:15]([CH3:14])[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:17]=3)[N:4]=[C:5]2[N:10]=[C:9]([CH3:11])[CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6933302-(Chloromethyl)-5,7-dimethylimidazo[1,2-a]pyrimidineHCID 201464331-Methyl-4-phenyl-1,3-dihydroimidazole-2-thione

Product 1

HCID 445487805,7-dimethyl-2-((1-methyl-4-phenyl-1H-imidazol-2-ylthio)methyl)imidazo[1,2-a]pyrimidineYield 468.6%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of 2-chloromethyl-5,7-dimethyl-imidazo[1,2-a]pyrimidine (1.55 g, 0.8 mmol), 1-methyl-4-phenyl-1,3-dihydro-imidazole-2-thione (1.5 g, 0.8 mmol) and K2CO3 (3.31 g, 2.4 mmol) in dry DMF (20 mL) was stirred under N2 at room temperature overnight. After removal of the solvent under vacuum, the residue was purified by preparative HPLC to afford the title compound (1.31 g, 47%) as a white solid. LC-MS: m/z=350.2 (MH+), tR=2.14 min, method D.

Workup

  1. customAfter removal of the solvent under vacuum
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-d7cdf4fa80d9427d895a7990bb57f76e
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08133897B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes