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Sodium hydride → (5-Ethyl-2,6-dimethoxy-pyrimidin-4-yl)-(3-hydroxymethyl-5-methyl-phenyl)-methanone

HRID 426185
ノート
印刷プレビュー

反応式

HRID 426185 の反応式
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:9]=[C:10]([CH:15]([C:18]2[C:23]([CH2:24][CH3:25])=[C:22]([O:26][CH3:27])[N:21]=[C:20]([O:28][CH3:29])[N:19]=2)C#N)[CH:11]=[C:12]([CH3:14])[CH:13]=1)(C)(C)C.[H-].[Na+].O.C1(C)C=CC(S(O)(=O)=[O:42])=CC=1>CN(C=O)C.CO>[CH2:24]([C:23]1[C:18]([C:15]([C:10]2[CH:11]=[C:12]([CH3:14])[CH:13]=[C:8]([CH2:7][OH:6])[CH:9]=2)=[O:42])=[N:19][C:20]([O:28][CH3:29])=[N:21][C:22]=1[O:26][CH3:27])[CH3:25]
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 3

HCID 24758Sodium hydrideHCID 521998p-Toluenesulfonic acid monohydrateHCID 178437280HCID 178437280、化合物

生成物 1

HCID 59184675(5-Ethyl-2,6-dimethoxy-pyrimidin-4-yl)-(3-hydroxymethyl-5-methyl-phenyl)-methanone収率 628.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 6228
Dimethylformamide
溶媒

実験手順

To a stirred solution of [3-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-phenyl]-(5-ethyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile (3.74 g, 8.47 mmol) in anhydrous DMF (40 ml), was added 60% sodium hydride (373 mg, 9.32 mmol). After 20 min., oxygen was bubbled into the reaction mixture for 3 hr. The mixture was partitioned between ether and aqueous saturated ammonium chloride solution. The ether layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was stirred with p-toluenesulfonic acid monohydrate (152 mg, 0.8 mmol) in methanol (10 ml) for 2 hr. at room temperature. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:1 to 3:2)) to afford 1.59 g (59%) of a white solid. m.p. 101-103° C.; 1H NMR (200 MHz, CDCl3) δ 1.05 (3H, t, J=7.4 Hz), 2.35-2.48 (5H, m), 3.93 (3H, s), 4.06 (3H, s), 4.63 (2H, br. S), 7.40 (1H, s), 7.56 (1H, s), 7.60 (1H, s).

後処理

  1. customoxygen was bubbled into the reaction mixture for 3 hr
  2. customThe mixture was partitioned between ether and aqueous saturated ammonium chloride solution
  3. washwashed with water twice
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customat room temperature
  8. customThe mixture was evaporated in vacuo
  9. customthe residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:1 to 3:2))

出典と根拠

ORDレコード
ord-f665b91ca31842808c998b0bf45f5ae2
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

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