Dichloromethane → 4-(3-Chloro-4-methoxybenzylamino)-5-(2-benzyloxyethoxycarbonyl)-6-chloro-2-methylthiopyrimidine

HRID 917639Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917639
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:5][NH:6][C:7]1[C:12]([C:13](Cl)=[O:14])=[C:11]([Cl:16])[N:10]=[C:9]([S:17][CH3:18])[N:8]=1.C(Cl)Cl.[CH2:27]([O:34][CH2:35][CH2:36][OH:37])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])O.[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:37][CH2:36][CH2:35][O:34][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:14])=[C:11]([Cl:16])[N:10]=[C:9]([S:17][CH3:18])[N:8]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 121412-(Benzyloxy) ethanolHCID 516892Sodium BicarbonateHCID 178482834-(3-Chloro-4-methoxybenzylamino)-5-chloroformyl-6-chloro-2-methylthiopyrimidine

Produkt 1

HCID 178483574-(3-Chloro-4-methoxybenzylamino)-5-(2-benzyloxyethoxycarbonyl)-6-chloro-2-methylthiopyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of whole amount of 4-(3-chloro-4-methoxybenzylamino)-5-chloroformyl-6-chloro-2-methylthiopyrimidine (prepared in the above (1)), methylene chloride 15 ml and 2-benzyloxyethanol 224 mg is refluxed for 30 minutes. After cooling the reaction mixture is diluted with water and neutralized with an aqueous saturated sodium hydrogen carbonate solution. The solution is washed with ethyl acetate. The methylene chloride layer is diluted with ethyl acetate, washed, dried and concentrated in vacuo. The residue is separated with silica gel chromatography (solvent; hexane:ethyl acetate=5:1) to give 4-(3-chloro-4-methoxybenzylamino)-5-(2-benzyloxyethoxycarbonyl)-6-chloro-2-methylthiopyrimidine as a colorless oil 655 mg.

Aufarbeitung

  1. temperatureis refluxed for 30 minutes
  2. temperatureAfter cooling the reaction mixture
  3. washThe solution is washed with ethyl acetate
  4. additionThe methylene chloride layer is diluted with ethyl acetate
  5. washwashed
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue is separated with silica gel chromatography (solvent; hexane:ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-80a90dea63d84750ada52c2c43e0d574
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273868B2

Notizen zur Reaktion

Wird geladen…