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Hydrochloric Acid → N'-(1-benzyl-4-methyl-5-nitro-6-oxopyrimidin-2-yl)-N,N-dimethylmethanimidamide

HRID 1805853
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1805853
[CH3:1][N:2]([CH3:16])/[CH:3]=[N:4]/[C:5]1[NH:6][C:7](=[O:15])[C:8]([N+:12]([O-:14])=[O:13])=[C:9]([CH3:11])[N:10]=1.C1CCN2C(=NCCC2)CC1.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>CN(C=O)C>[CH2:28]([N:6]1[C:7](=[O:15])[C:8]([N+:12]([O-:14])=[O:13])=[C:9]([CH3:11])[N:10]=[C:5]1/[N:4]=[CH:3]/[N:2]([CH3:1])[CH3:16])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 1355361192-[(Dimethylamino)methylene]amino-6-methyl-5-nitro-4-pyrimidinol

Produkt 1

HCID 11186127N'-(1-benzyl-4-methyl-5-nitro-6-oxopyrimidin-2-yl)-N,N-dimethylmethanimidamideAusbeute 85.493,203 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of (E)-N,N-Dimethyl-N′-(4-methyl-5-nitro-6-oxo-1,6-dihydropyrimidin-2-yl)formimidamide (53.4 g, 0.24 mmol) in DMF (690 mL) was added DBU (44.6 mL, 0.30 mol) and benzyl bromide (44.4 mL, 0.29 mol) and stirred at room temperature for 1 h. The excess of DBU was neutralized with HCl, and the mixture was concentrated in vacuo. The residue was dissolved in methylene chloride and extracted twice with 2M HCl and water, then dried over Na2SO4 and concentrated. Trituration with ethanol afforded the crystalline product which was washed with ethanol to give the product (64.7 g, 86% yield) and used in the next step without further purification.

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. extractionextracted twice with 2M HCl and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customTrituration with ethanol afforded the crystalline product which
  7. washwas washed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-a8dfdfc86cc24ba1922c4c63fc31ad53
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08354532B2

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