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

HRID 537897Notes

Reaction equation

HRID 537897 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

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 6228DimethylformamideSolvent

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-7d5848a814ea4d5bafe4dae2bafc176b
Source dataset
uspto-grants-2014_10
Patent number
US08865711B2

Reaction notes

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