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Sodium hydride → 4,4-Dimethyl-2-phenyl-1,2,3,4-tetrahydro-pyrrolo[1,2-a]pyrimidine-8-carboxylic acid ethyl ester

HRID 2108584
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2108584
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][NH:8][C:7]=1[NH2:11])=[O:5])[CH3:2].[H-].[Na+].[CH3:14][C:15]([CH3:25])=[CH:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O.[BH4-].[Na+]>CN(C=O)C.CCOC(C)=O.CCO>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][N:8]2[C:15]([CH3:25])([CH3:14])[CH2:16][CH:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:11][C:7]=12)=[O:5])[CH3:2]
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Komponenten

8

Edukt 4

HCID 24758Sodium hydrideHCID 976742-Buten-1-one, 3-methyl-1-phenyl-HCID 4311764Sodium borohydrideHCID 12111022Ethyl 2-amino-1H-pyrrole-3-carboxylate

Produkt 1

HCID 576321734,4-Dimethyl-2-phenyl-1,2,3,4-tetrahydro-pyrrolo[1,2-a]pyrimidine-8-carboxylic acid ethyl esterAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Compound 1 (0.68 g, 4.41 mmol) was dissolved in DMF (5 mL). NaH (60% in mineral oil, 0.19 g, 4.7 mmol) was added at room temperature affording rapid gas evolution. The reaction stirred for 0.5 h upon which 3-methyl-1-phenyl-but-2-en-1-one (0.50 g, 3.15 mmol) was added. The reaction stirred for 0.5 h upon which EtOH (5 mL) and NaBH4 (1.19 g) were added. The solution was brought to 60° C. for 0.5 h. and then cooled to room temperature. The solution was quenched with water, extracted with Et2O (3 times), dried (Na2SO4) and concentrated. Flash chromatography (10% AcOEt) to give the desired product as a tan solid (0.60 g, 63% yield). MS Calcd.: 298. Found 299 (M+H).

Aufarbeitung

  1. customaffording rapid gas evolution
  2. additionwas added
  3. additionwere added
  4. customThe solution was quenched with water
  5. extractionextracted with Et2O (3 times)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-15d1448a072041c390e1cca918769156
Quelldatensatz
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07514441B2

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