Ethanol → 4,6-Dichloro-N-[(4-methoxyphenyl)methyl]pyrimidin-2-amine

HRID 1368774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1368774
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.C(O)C.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.P(=O)(O)(O)O>C(Cl)Cl>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([NH:20][CH2:19][C:18]2[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[N:3]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 1004Phosphoric AcidHCID 754524-Methoxybenzylamine2×HCID 773782,4,6-Trichloropyrimidine

Produkt 1

HCID 132301344,6-Dichloro-N-[(4-methoxyphenyl)methyl]pyrimidin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 27.5 g portion of 2,4,6-trichloropyrimidine was suspended in a mixed solvent of 200 ml ethanol and 200 ml methylene chloride, to which, under ice-cooling, was subsequently added dropwise 30 ml of 4-methoxybenzylamine. After 19 hours of stirring at the same temperature, 10 ml of 4-methoxybenzylamine was further added dropwise and the mixture was stirred for 18 hours. The reaction solution was mixed with 200 ml of 0.5 N phosphoric acid aqueous solution and extracted with chloroform, and then the organic layer was washed with saturated brine. After drying with anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure, and the thus obtained residue was applied to a silica gel chromatography and developed with a chloroform-hexane (3:1) mixed solvent to obtain 13.3 g of 4,6-dichloro-2-(4-methoxybenzyl)aminopyrimidine and further developed with a chloroform-ethyl acetate (1:3) mixed solvent to obtain 24.2 g of 2,6-dichloro-4-(4-methoxybenzyl)aminopyrimidine. 2,6-Dichloro-4-(4-methoxybenzyl)aminopyrimidine

Aufarbeitung

  1. temperaturecooling
  2. additionwas further added dropwise
  3. extractionextracted with chloroform
  4. washthe organic layer was washed with saturated brine
  5. dry with materialAfter drying with anhydrous sodium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. additionmixed solvent

Quellen und Nachweise

ORD-Eintrag
ord-aecb3be46d584f14a07749a95e25f6e3
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06573377B1

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