Dimethylformamide → 3-(7-Hydroxy-2,4-dimethoxy-5,5-dimethyl-5,7-dihydro-furo[3,4-d]pyrimidin-7-yl)-5-methyl-benzonitrile

HRID 426283ノート

反応式

HRID 426283 の反応式
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH3:12])[CH:11]=1)[C:7]#[N:8])#[N:2].ClC1[C:19]([C:20]([OH:23])([CH3:22])[CH3:21])=[C:18]([O:24][CH3:25])[N:17]=[C:16]([O:26][CH3:27])N=1.[H-].[Na+].CN(C=[O:34])C>>[OH:34][C:3]1([C:4]2[CH:5]=[C:6]([CH:9]=[C:10]([CH3:12])[CH:11]=2)[C:7]#[N:8])[C:1]2[N:2]=[C:16]([O:26][CH3:27])[N:17]=[C:18]([O:24][CH3:25])[C:19]=2[C:20]([CH3:22])([CH3:21])[O:23]1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 237307032-(4-Chloro-2,6-dimethoxy-pyrimidin-5-yl)-propan-2-olHCID 667054463-(Cyanomethyl)-5-methylbenzonitrile

生成物 1

HCID 591846603-(7-Hydroxy-2,4-dimethoxy-5,5-dimethyl-5,7-dihydro-furo[3,4-d]pyrimidin-7-yl)-5-methyl-benzonitrile収率 18%

反応条件

温度
0 °C

実験手順

3-Cyanomethyl-5-methyl-benzonitrile (0.067 g, 0.432 mmol) and 2-(4-Chloro-2,6-dimethoxy-pyrimidin-5-yl)-propan-2-ol (0.100 g, 0.432 mmol) was dissolved in DMF (1.5 mL) and cooled to 0° C. 60% Sodium hydride (0.035 g, 0.64 mmol) was added portionwise and the reaction was stirred at 0° C. for 1 h, then rt overnight. The reaction was quenched with 1N HCl, extracted with ethyl acetate and washed with saturated ammonium chloride solution. Organic layer was dried (MgSO4) and concentrated and purified by flash column chromatography (silica gel, 0 to 40% ethyl acetate/hexane) to give a white solid (0.027 g, 18%). 1H NMR (300 MHz, CDCl3): δ 7.80 (s, 2H), 7.39 (s, 1H), 4.01 (s, 3H), 3.93 (s, 3H), 2.37 (s, 3H), 1.66 (s, 3H), 1.63 (s, 3H). Mass spectrum: 342.3 (M+H)+.

後処理

  1. customrt overnight
  2. customThe reaction was quenched with 1N HCl
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated ammonium chloride solution
  5. dry with materialOrganic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel, 0 to 40% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-b167f60d3dbd4584b4886a3d9f0e1443
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

反応ノート

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