Methyl 5-(benzyloxy)-1-methyl-2-(methylsulfonyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate → 5-Benzyloxy-2-cyclohexylmethyl-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid methyl ester

HRID 1409596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1409596
[CH:1]1([CH2:7][Mg]Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:10][O:11][C:12]([C:14]1[N:15]=[C:16](S(C)(=O)=O)[N:17]([CH3:29])[C:18](=[O:28])[C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13]>C1COCC1>[CH3:10][O:11][C:12]([C:14]1[N:15]=[C:16]([CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:17]([CH3:29])[C:18](=[O:28])[C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13]

Komponenten

4

Edukt 2

HCID 86710287Methyl 5-(benzyloxy)-1-methyl-2-(methylsulfonyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylateHCID 178419664HCID 178419664, Verbindung

Produkt 1

HCID 867102965-Benzyloxy-2-cyclohexylmethyl-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid methyl esterAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Cyclohexylmethylmagnesium bromide solution (1.77 ml; 885 μM of 0.5M solution in THF) was added dropwise to a solution of 5-benzyloxy-2-methanesulfonyl-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl ester (0.26 g; 738 μM) in THF (10 ml). After stirring at room temperature for 1 h, the reaction mixture was quenched by the addition of saturated ammonium chloride solution. The product was extracted into EtOAc, washed with brine, dried (Na2SO4) and evaporated to dryness under reduced pressure to give the title product as a colourless oil (0.040 g; 70%). LCMS: m/z=367 (MH+).

Aufarbeitung

  1. customthe reaction mixture was quenched by the addition of saturated ammonium chloride solution
  2. extractionThe product was extracted into EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7a8cd4a0789144718e3ec847629f597e
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921388B2

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