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Sodium hydride → 3-[(2,6-Bis-benzyloxy-5-tert-butyl-pyrimidin-4-yl)-cyano-methyl]-5-methyl-benzonitrile

HRID 426130
ノート
印刷プレビュー

反応式

HRID 426130 の反応式
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([C:23]([CH3:26])([CH3:25])[CH3:24])=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([C:30]1[CH:31]=[C:32]([CH2:37][C:38]#[N:39])[CH:33]=[C:34]([CH3:36])[CH:35]=1)#[N:29].[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[N:10]=[C:11]([CH:37]([C:38]#[N:39])[C:32]2[CH:31]=[C:30]([CH:35]=[C:34]([CH3:36])[CH:33]=2)[C:28]#[N:29])[C:12]([C:23]([CH3:26])([CH3:25])[CH3:24])=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 591848352,4-Bis-benzyloxy-5-tert-butyl-6-chloro-pyrimidineHCID 667054463-(Cyanomethyl)-5-methylbenzonitrile

生成物 1

HCID 591847533-[(2,6-Bis-benzyloxy-5-tert-butyl-pyrimidin-4-yl)-cyano-methyl]-5-methyl-benzonitrile収率 30%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

To a stirred mixture of 2,4-Bis-benzyloxy-5-tert-butyl-6-chloro-pyrimidine (3.8 g, 10 mmol) and 3-cyano-5-methylphenyl acetonitrile (1.56 g, 10 mmol) in anhydrous DMF (20 ml) at 0° C. (ice bath) under nitrogen atmosphere, was portionwise added 60% sodium hydride (880 mg, 22 mmol). After stirring for 1 hr., the mixture was further stirred at room temperature for overnight. The mixture was then neutralized with aqueous saturated ammonium chloride solution and the crude product was extracted with ether and purified by silica gel column chromatography (eluent, EA:hexanes (1:10)) to afford 1.48 g (30%) of the title compound as a colorless syrup. m.p. 126-128° C.; 1H NMR (200 MHz, CDCl3) δ 1.46 (9H, s), 2.36 (3H, s), 5.29 (1H, d, J=12.2 Hz), 5.38 (1H, d, J=12.2 Hz), 5.46 (2H, s), 5.98 (1H, s), 7.22-7.46 (10H, m); m/z (EI) 502 (M+).

後処理

  1. stirring, the mixture was further stirred at room temperature for overnight
  2. extractionthe crude product was extracted with ether
  3. custompurified by silica gel column chromatography (eluent, EA:hexanes (1:10))

出典と根拠

ORDレコード
ord-40faf8a89ea84184966f7422221480de
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08106064B2

反応ノート

読み込み中…

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