Morpholine → 4-(6-Chloropyrimidin-4-yl)morpholine

HRID 594054

Reaktionsgleichung

Reaktionsgleichung von HRID 594054
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C(N(CC)CC)C>CCO>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 709434,6-Dichloropyrimidine

Produkt 1

HCID 7960704-(6-Chloropyrimidin-4-yl)morpholineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4,6-dichloropyrimidine (1.0 equiv.) in EtOH (0.44 M) was added morpholine (1.0 equiv.) followed by triethylamine (1.10 equiv.). The resulting mixture was stirred at RT for 16 hours. The reaction mixture was then concentrated in vacuo and dried under high vacuum over 20 h to yield 4-(6-chloropyrimidin-4-yl)morpholine as a white solid in 93% yield. LCMS (m/z) (M+H)=200.0/201.8, Rt=0.35 min. 1H NMR (400 MHz, <cdcl3>) δ ppm 3.53-3.71 (m, 4H) 3.72-3.83 (m, 4H) 6.51 (s, 1H) 8.39 (s, 1H) 11.75 (br. s., 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customdried under high vacuum over 20 h

Quellen und Nachweise

ORD-Eintrag
ord-e9f4c71f8d474a7d929dd8217a406dec
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242969B2

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