3-(Bromomethyl)biphenyl → 3-benzyl-6-(biphenyl-3-ylmethylsulfanyl)-5-methyl-1H-pyrimidine-2,4-dione

HRID 1373054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373054
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([SH:16])[NH:10][C:9]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[CH2:27]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([S:16][CH2:27][C:26]2[CH:25]=[C:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:31]=[CH:30][CH:29]=2)[NH:10][C:9]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 38644053-(Bromomethyl)biphenylHCID 210740613-Benzyl-6-mercapto-5-methyl-1H-pyrimidine-2,4-dione

Produkt 1

HCID 210739963-benzyl-6-(biphenyl-3-ylmethylsulfanyl)-5-methyl-1H-pyrimidine-2,4-dioneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

3-Benzyl-6-mercapto-5-methyl-1H-pyrimidine-2,4-dione (0.25 g, 1.0 mmol) was dissolved in dimethylformamide (10 mL). 3-Phenylbenzyl bromide (0.25 g, 1.02 mmol) was added and the reaction heated at 60° C. for 2 hours. The dimethylformamide was removed in vacuo. The residue was purified by flash chromatography on silica gel eluting with hexane:ethyl acetate (3:1) to give 3-benzyl-6-(biphenyl-3-ylmethylsulfanyl)-5-methyl-1H-pyrimidine-2,4-dione (0.41 g, 99% yield). MS (APCI+), m/z (%): 415(100), 413 (30), 247(100).

Aufarbeitung

  1. customThe dimethylformamide was removed in vacuo
  2. customThe residue was purified by flash chromatography on silica gel eluting with hexane:ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-5a9712bc09884e578785e79ac33b0df1
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07160893B2

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