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 570951ノート

反応式

HRID 570951 の反応式
[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

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178456698HCID 178456698、化合物

生成物 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)-one収率 89%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8d0c7066e7f74cb5bf8e14662e70540a
出典データセット
uspto-grants-2015_05
特許番号
US09024018B2

反応ノート

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