Potassium Carbonate → HCID 178429521, compound

HRID 630078Notes

Reaction equation

HRID 630078 reaction equation
Cl.[Cl:2][C:3]1[N:7]([CH3:8])[C:6]([CH2:9]Cl)=[N:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][C:18]1[N:23]=[C:22]([SH:24])[N:21]=[C:20]([OH:25])[CH:19]=1>CC(C)=O>[Cl:2][C:3]1[N:7]([CH3:8])[C:6]([CH2:9][S:24][C:22]2[N:21]=[C:20]([OH:25])[CH:19]=[C:18]([CH3:17])[N:23]=2)=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123115195-chloro-2-(chloromethyl)-1-methyl-1H-imidazole hydrochlorideHCID 178429541HCID 178429541, compound

Product 1

HCID 178429521HCID 178429521, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-chloro-2-(chloromethyl)-1-methyl-1H-imidazole hydrochloride (1.0 g, 5.0 mmol), potassium carbonate (1.65 g, 12 mmol), and 6-methyl-2-sulfanylpyrimidin-4-ol (560 mg, 4.0 mmol) were mixed in acetone (20 mL). The mixture was stirred at room temperature overnight. Acetone was then removed under reduced pressure. The crude solid was purified by column chromatography to provide the title compound as a white solid (850 mg, 79% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 3.60 (s, 3H), 4.51 (s, 2H), 6.04 (br, 1H), 6.93 (s, 1H); M+271.

Workup

  1. customAcetone was then removed under reduced pressure
  2. customThe crude solid was purified by column chromatography

Sources & evidence

ORD record
ord-9bed9c80a61c42b2857b9c913024126f
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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