Water → DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(sec-amyloxy)benzyl]aminopyrimidine

HRID 330313

Reaktionsgleichung

Reaktionsgleichung von HRID 330313
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[Cl:25][C:26]1[N:31]=[C:30]([NH:32][CH:33]([CH2:41][CH3:42])[C:34]2[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1.[Na].Br[CH:47]([CH2:49][CH2:50][CH3:51])[CH3:48].O>CN(C)C=O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[Cl:25][C:26]1[N:31]=[C:30]([NH:32][CH:33]([CH2:41][CH3:42])[C:34]2[CH:39]=[CH:38][C:37]([O:40][CH:47]([CH2:49][CH2:50][CH3:51])[CH3:48])=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 78902-BromopentaneHCID 5360545SodiumHCID 131716268DL-5 Chloro-6-ethyl-4-(alphaethyl-4-hydroxybenzylamino)pyrimidine

Produkt 1

HCID 131716266DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(sec-amyloxy)benzyl]aminopyrimidineAusbeute 32,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1.1 g of dl-5-chloro-6-ethyl-4-(α-ethyl-4-hydroxybenzyl)aminopyrimidine.sodium salt dissolved in 30 ml of N,N-dimethylformamide was added 0.6 g of 2-bromopentane, and the mixture was stirred at 90° to 100° C. for 8 hours. After completion of the reaction, the reaction mixture was poured into water and separated oily product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and ethyl acetate was distilled off under reduced pressure. The oily product obtained was isolated by column chromatography (Wako Gel C-200, trade name, eluted with toluene:ethyl acetate=7:1) to give 0.4 g of the desired product as pale yellow liquid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customseparated oily product
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate and ethyl acetate
  6. distillationwas distilled off under reduced pressure
  7. customThe oily product obtained

Quellen und Nachweise

ORD-Eintrag
ord-ef61755fe23349e799366bd7cd7d9630
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04895849

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