4,6-Dichloropyrimidine → 6-Chloro-N-(4-methoxybenzyl)pyrimidin-4-amine

HRID 2373947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2373947
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C>CCCCO>[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:16][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=2)=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 709434,6-DichloropyrimidineHCID 754524-MethoxybenzylamineHCID 81531Diisopropylethylamine

Produkt 1

HCID 223094976-Chloro-N-(4-methoxybenzyl)pyrimidin-4-amineAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 4,6-dichloropyrimidine (Aldrich, 3.6 g, 24.2 mmol), 4-methoxybenzylamine (2.7 g, 19.7 mmol), DIPEA (5 ml, 28.8 mmol), and n-BuOH was heated at reflux for 3 h. The mixture was concentrated and the residue treated with H2O (150 mL) and EtOAc (175 mL). The EtOAc phase was separated, washed with saturated aq. NaHCO3 solution and brine, dried (MgSO4), and concentrated to give the title compound (4.5 g) which was used without further purification. 1H NMR (DMSO-d6) δ 8.29 (s, 1H), 8.13 (br s, 1H), 7.25 (d, 2H, J=8.2 Hz), 6.90 (d, 2H, J=8.2 Hz), 6.56 (s, 1H), 4.48 (s, 2H), 3.75 (s, 3H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. concentrationThe mixture was concentrated
  4. additionthe residue treated with H2O (150 mL) and EtOAc (175 mL)
  5. customThe EtOAc phase was separated
  6. washwashed with saturated aq. NaHCO3 solution and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-00c5073b629944198f8b25052d84e059
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07459562B2

Notizen zur Reaktion

Wird geladen…