4,6-Dichloro-2-methyl-5-nitropyrimidine → (6-Chloro-2-methyl-5-nitro-pyrimidin-4-yl)(2,4,6-trimethyl-pyridin-3-yl)amine

HRID 968035

Reaktionsgleichung

Reaktionsgleichung von HRID 968035
[CH3:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([Cl:12])[N:3]=1.[CH3:13][C:14]1[C:19]([NH2:20])=[C:18]([CH3:21])[CH:17]=[C:16]([CH3:22])[N:15]=1>C(#N)C>[Cl:12][C:4]1[N:3]=[C:2]([CH3:1])[N:7]=[C:6]([NH:20][C:19]2[C:14]([CH3:13])=[N:15][C:16]([CH3:22])=[CH:17][C:18]=2[CH3:21])[C:5]=1[N+:9]([O-:11])=[O:10]

Komponenten

4

Edukt 2

HCID 831924,6-Dichloro-2-methyl-5-nitropyrimidineHCID 988462,4,6-Trimethyl-3-pyridinamine

Produkt 1

HCID 10757155(6-Chloro-2-methyl-5-nitro-pyrimidin-4-yl)(2,4,6-trimethyl-pyridin-3-yl)amineAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 2-methyl-5-nitro-4,6-dichloro-pyrimidine (208 mg, 1.00 mmol) in 2.5 ml of acetonitrile was treated with 2,4,6-trimethyl-3-amino-pyridine (273 mg, 2 mmol) stirred at room temperature 2 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give red residue. The residue was purified through silica gel column chromatography using chloroform to 6% methanol in chloroform as eluent to give the title compound (110 mg, 36%) as an orange oil. 1H NMR (CDCl3) δ 8.78 (brs, 1H), 6.97 (s, 1H), 2.54 (s, 3H), 2.43 (s, 3H), 2.40 (s, 3H), 2.17 (s, 3H) ppm.

Aufarbeitung

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give red residue
  7. customThe residue was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0e9fba5a5f63499687f42bc9ebd40717
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956047B1

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