4,6-Dichloropyrimidine → HCID 58940650, Verbindung

HRID 548934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 548934
[C:1]([O:5][C:6](=[O:13])[N:7]([CH:9]1[CH2:12][NH:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:20]=[C:19](Cl)[N:18]=[CH:17][N:16]=1>CC(O)C>[Cl:14][C:15]1[N:16]=[CH:17][N:18]=[C:19]([N:11]2[CH2:12][CH:9]([N:7]([CH3:8])[C:6](=[O:13])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:10]2)[CH:20]=1

Komponenten

4

Edukt 2

HCID 709434,6-DichloropyrimidineHCID 23033645tert-Butyl azetidin-3-yl(methyl)carbamate

Produkt 1

HCID 58940650HCID 58940650, VerbindungAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Azetidin-3-yl-methyl-carbamic acid tert-butyl ester (1.97 g, 11 mmol) in IPA (5 mL) was added dropwise to a stirred solution of 4,6-dichloropyrimidine (1.49 g, 10 mmol) in IPA (20 mL) followed by dropwise addition of TEA (2.11 mL, 15.1 mmol) at ambient temperature under N2. The resulting milky yellow solution was heated to 80° C. and maintained at 80° C. for 2 hours. The solution was allowed to cool and evaporated to give a yellow oil. The crude material was partitioned between DCM (70 mL) and water (30 aqueous extract was re-extracted with DCM (70 mL). The combined organic extract was washed with saturated aqueous sodium bicarbonate (30 mL), dried (MgSO4), filtered and evaporated to give a coloured oil. The crude oil was purified by flash column chromatography on silica gel eluting with DCM:MeOH (99:1 changing to 96:4 by volume) to yield the title compound as a solid (1.93 g, 64%).

Aufarbeitung

  1. temperaturemaintained at 80° C. for 2 hours
  2. temperatureto cool
  3. customevaporated
  4. customto give a yellow oil
  5. customThe crude material was partitioned between DCM (70 mL) and water (30
  6. extractionaqueous extract
  7. extractionwas re-extracted with DCM (70 mL)
  8. extractionThe combined organic extract
  9. washwas washed with saturated aqueous sodium bicarbonate (30 mL)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customevaporated
  13. customto give a coloured oil
  14. customThe crude oil was purified by flash column chromatography on silica gel eluting with DCM:MeOH (99:1 changing to 96:4 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-2b3e615683a543daaedf44ac0c9895af
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943628B2

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