Sodium Hydroxide → 4,6-Diamino-5-(1,2-bis(4-isopropylphenyl)ethenyl)pyrimidine

HRID 378246

反応式

HRID 378246 の反応式
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:3].[B]1OC2C(=CC=CC=2)O1.[NH2:30][C:31]1[C:36](I)=[C:35]([NH2:38])[N:34]=[CH:33][N:32]=1.C(=O)(O)[O-].[Na+].[OH-].[Na+]>C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:30][C:31]1[C:36]([C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:2]([CH3:1])[CH3:3])=[CH:5][CH:6]=2)=[CH:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:17]=2)=[C:35]([NH2:38])[N:34]=[CH:33][N:32]=1

参加物

9

反応物 5

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 6327445BenzcatechinboraneHCID 112540441,2-Bis(4-(2-propyl)phenyl)acetyleneHCID 113109004,6-Pyrimidinediamine, 5-iodo-

生成物 1

HCID 536772854,6-Diamino-5-(1,2-bis(4-isopropylphenyl)ethenyl)pyrimidine収率 28%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

1,2-Bis(4-(2-propyl)phenyl)acetylene (11.40 g, 43 mmol) was dissolved in 50 mL THF, catecholborane (1 M, 50 mL) in THF was added, and the mixture was heated at reflux for 30 hours. The mixture was cooled, then 4,6-diamino-5-iodo-pyrimidine, 30 mL saturated aqueous sodium bicarbonate, 20 mL 3N aqueous sodium hydroxide, and 1.00 g (0.87 mmol) tetrakis(triphenylphosphine)palladium(0) were added. The mixture was heated to reflux for 18 hours, cooled, diluted with water, then extracted with ethyl acetate. The organic layers were combined, dried with magnesium sulfate, and the solvent evaporated. The residue was chromatographed on silica gel with 2.5% to 5% (19:1 ethanol:ammonium hydroxide) in ethyl acetate to give the desired product (4.53 g, 28% yield).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 hours
  3. temperatureThe mixture was cooled
  4. temperatureThe mixture was heated
  5. temperatureto reflux for 18 hours
  6. temperaturecooled
  7. extractionextracted with ethyl acetate
  8. dry with materialdried with magnesium sulfate
  9. customthe solvent evaporated
  10. customThe residue was chromatographed on silica gel with 2.5% to 5% (19:1 ethanol:ammonium hydroxide) in ethyl acetate

出典と根拠

ORDレコード
ord-758c379a3dcf468f97ba429b58b3c21e
出典データセット
uspto-grants-2000_02
特許番号
US06030969

関連ノート

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