Sodium hydride → Methyl 5-methyl-4-oxo-3-(2-(2-oxopyrrolidin-1-yl)ethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

HRID 1094737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094737
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].[H-].[Na+].CS(O[CH2:23][CH2:24][N:25]1[CH2:29][CH2:28][CH2:27][C:26]1=[O:30])(=O)=O>CN(C=O)C>[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:23][CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][C:26]3=[O:30])[CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 725279Methyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylateHCID 446271162-(2-Oxopyrrolidin-1-yl)ethyl methanesulfonate

Produkt 1

HCID 59842882Methyl 5-methyl-4-oxo-3-(2-(2-oxopyrrolidin-1-yl)ethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylateAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate (0.8 g, 3.5 mmol) in DMF (10 ml) was added NaH (0.28 g, 7 mmol) followed by the addition of 2-(2-oxopyrrolidin-1-yl)ethyl methanesulfonate (0.7 g, 3.5 mmol). The mixture was then stirred overnight at RT. Reaction was quenched with water (10 ml) and mixture extracted with ethyl acetate. Ethyl acetate layer was separated, dried over anhydrous sodium sulfate and evaporated to yield 0.5 g of methyl 5-methyl-4-oxo-3-(2-(2-oxopyrrolidin-1-yl)ethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate, as an oil (yield: 42.8%).

Aufarbeitung

  1. customReaction
  2. customwas quenched with water (10 ml) and mixture
  3. extractionextracted with ethyl acetate
  4. customEthyl acetate layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5bf84413c1924dd0a07d7a93e565319b
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133998B2

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