2-cyclopentyl-6-ethylpyrimidin-4(3H)-one → 4-Chloro-2-cyclopentyl-6-ethylpyrimidine

HRID 1508929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1508929
O(Cl)[Cl:2].[P+5].[CH:5]1([C:10]2[NH:15][C:14](=O)[CH:13]=[C:12]([CH2:17][CH3:18])[N:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1>[OH-].[Na+]>[Cl:2][C:14]1[CH:13]=[C:12]([CH2:17][CH3:18])[N:11]=[C:10]([CH:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)[N:15]=1

Komponenten

4

Edukt 2

HCID 1360851072-cyclopentyl-6-ethylpyrimidin-4(3H)-oneHCID 178479711HCID 178479711, Verbindung

Produkt 1

HCID 609214014-Chloro-2-cyclopentyl-6-ethylpyrimidineAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Phosphorus(V) oxychloride (150 g, 99.0 mmol) was slowly added to 2-cyclopentyl-6-ethylpyrimidin-4(3H)-one (18.9 g, 98.3 mmol) at 0° C. Then, the reaction mixture was warmed to 100° C. for 3 h. After this time, the mixture was cooled, diluted with sodium hydroxide, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/dichloromethane) to afford the title compound (5.1 g, 57%) as yellow oil. MW=210.70. 1H NMR (CDCl3, 300 MHz) δ 7.01 (s, 1H), 3.36-3.20 (m, 1H), 2.74 (q, J=7.5 Hz, 2H), 2.14-1.99 (m, 2H), 1.98-1.76 (m, 4H), 1.75-1.63 (m, 2H), 1.29 (t, J=7.5 Hz, 3H); APCI MS m/z 211 [M+H]+.

Aufarbeitung

  1. temperatureAfter this time, the mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica, hexanes/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-252381d0f4b64e1d8bdcf79e55672179
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221843B2

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