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Methyl iodide → 3,4-Diaminopyridine

HRID 967979
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 967979
[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[NH2:24])[CH2:4][CH3:5])[CH3:2].[Li]N([Si](C)(C)C)[Si](C)(C)[CH3:28].CI>C1COCC1>[N:10]1[CH:11]=[CH:12][C:7]([NH2:6])=[C:8]([NH2:24])[CH:9]=1.[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[NH:24][CH3:28])[CH2:4][CH3:5])[CH3:2]
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Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 219121512-(2,4,6-trimethylphenoxy)-N4-(1-ethylpropyl)-6-methyl-pyridine-3,4-diamineHCID 178418261HCID 178418261, Verbindung

Produkt 2

HCID 59183,4-DiaminopyridineHCID 21912312N4-(1-ethyl-propyl)-6,N3-dimethyl-2-(2,4,6-trimethyl-phenoxy)-pyridine-3,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of N4-(1-ethyl-propyl)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridine-3,4-diamine (0.250 g, 0.763 mmol) in dry THF (6 ml) was treated with 1M LiN(SiMe3)2 in THF (1.0 ml, 1.0 mmol) at −78° C. and stirred for 10 min. an excess of methyl iodide was added and the resulting mixture was stirred at room temperature overnight. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give a crude material. The crude material was purified through silica gel column chromatography using 5% ethyl acetate in hexane as eluent to give N4-(1-ethyl-propyl)-6,N3,N3-trimethyl-2,4,6-trimethyl-phenoxy)-pyridine-3,4-diamine and N4-(1-ethyl-propyl)-6,N3-dimethyl-2-(2,4,6-trimethyl-phenoxy)-pyridine-3,4-diamine.

Aufarbeitung

  1. additionwas added
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customto give a crude material
  7. customThe crude material was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b9fcad36dba14aeeb4a5b96506198056
Quelldatensatz
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06956047B1

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