Methyl iodide → 8-(1-Methyl-4-phenyl-1H-imidazol-2-yl)-3-(prop-2-ynyl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one

HRID 570951Notes

Reaction equation

HRID 570951 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12]3[N:13]=[CH:14][N:15]4[C:20](=[O:21])[N:19]([CH2:22][C:23]#[CH:24])[N:18]=[N:17][C:16]=34)[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:27]I>CN(C=O)C>[CH3:27][N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[C:9]1[C:12]1[N:13]=[CH:14][N:15]2[C:20](=[O:21])[N:19]([CH2:22][C:23]#[CH:24])[N:18]=[N:17][C:16]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178456698HCID 178456698, compound

Product 1

HCID 498694228-(1-Methyl-4-phenyl-1H-imidazol-2-yl)-3-(prop-2-ynyl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-oneYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-(4-Phenyl-1H-imidazol-2-yl)-3-(prop-2-ynyl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one (1.07 mmol) was dissolved in dry DMF (35 mL) and cooled in ice under a nitrogen atmosphere. A 60% suspension of sodium hydride in mineral oil (1.18 mmol) was added in one portion and the reaction stirred on ice for 10 minutes. Methyl iodide (2.14 mmol) was then added dropwise to the reaction and the mixture stirred at room temperature for 48 hours. The mixture was poured onto ice water (140 mL) and the precipitate was filtered, washed with water, ethyl acetate, and diethyl ether, and purified by column chromatography (hexane:ethyl acetate 4:3) to give the title compound (0.030 g; 89%). δH (DMSO-d6) 8.97 (1H, s), 7.90 (1H, s), 7.83 (2H, d, J=7.2), 7.40 (2H, t, J=7.6), 7.25 (1H, t, J=7.2), 5.13 (2H, d, J=2.0), 3.99 (3H, s), 3.52 (1H, J=2.0).

Workup

  1. temperaturecooled in ice under a nitrogen atmosphere
  2. stirringthe mixture stirred at room temperature for 48 hours
  3. additionThe mixture was poured onto ice water (140 mL)
  4. filtrationthe precipitate was filtered
  5. washwashed with water, ethyl acetate, and diethyl ether
  6. custompurified by column chromatography (hexane:ethyl acetate 4:3)

Sources & evidence

ORD record
ord-8d0c7066e7f74cb5bf8e14662e70540a
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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