Methyl iodide → HCID 20751408, compound

HRID 2238631Notes

Reaction equation

HRID 2238631 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[N:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1)=O.[NH2:17][C:18]([NH2:20])=[S:19].[CH3:21][O-].[Na+].CI>C(O)CCC>[CH3:21][S:19][C:18]1[N:20]=[C:5]([C:7]2[N:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[CH:3][N:17]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 2723790ThioureaHCID 10942334Sodium MethoxideHCID 59176797HCID 59176797, compound

Product 1

HCID 20751408HCID 20751408, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
85 °C

Procedure

1 g of (E)-3-(dimethylamino)-1-imidazo[1,2-a]pyridin-3-yl-2-propen-1-one [1-2] was dissolved in 10 mL of n-butanol, then 354 mg of thiourea and 377 mg of sodium methoxide were added, and the mixture was stirred at 85° C. for 2 hours. After cooling back to the room temperature, 868 μL of methyl iodide was added, and stirred at room temperature for 30 minutes. The solvent was distilled off until the volume is halved, the solid thus produced was taken and washed with diethyl ether and with water in the subsequent order, and then dried under reduced pressure to obtain 728 mg of 3-[2-methylthio-4-pyrimidinyl]imidazo[1,2-a]pyridine [1-3] as a grey solid.

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 30 minutes
  3. distillationThe solvent was distilled off until the volume
  4. customthe solid thus produced
  5. washwashed with diethyl ether and with water in the subsequent order
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-df210168c0fb47bfb2c8f3e98cc495e8
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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