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

HRID 426283Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426283
[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

Komponenten

5

Edukt 4

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

Produkt 1

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

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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)+.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b167f60d3dbd4584b4886a3d9f0e1443
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106064B2

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