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

HRID 426130
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HRID 426130 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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+).

후처리

  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))

출처 및 근거

ORD 기록
ord-40faf8a89ea84184966f7422221480de
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08106064B2

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