1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(Azidomethyl)-2-methylpyrimidine

HRID 657748

Reaktionsgleichung

Reaktionsgleichung von HRID 657748
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][N:3]=1.C1C=CC(OP(OC2C=CC=CC=2)([N:19]=[N+:20]=[N-:21])=O)=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.C(Cl)Cl.O>[N:19]([CH2:8][C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[N:7][CH:6]=1)=[N+:20]=[N-:21]

Komponenten

7

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 14686706(2-Methylpyrimidin-5-yl)methanol

Produkt 1

HCID 545950225-(Azidomethyl)-2-methylpyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of (2-methylpyrimidin-5-yl)methanol (0.82 g, 6.6 mmol) in toluene (30 mL) and methylene chloride (40 mL) at 0° C. was treated with diphenylphosphonic azide (2.8 mL, 13 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (2.0 mL, 13 mmol) and stirred at 0° C. for 2 h. After being further stirred at rt for 16 h, the reaction mixture was diluted with water (50 mL) and methylene chloride (50 mL). The organic layer was separated and washed with brine, dried (Mg2SO4), filtered, and concentration. The residue was purified by silica gel column to yield a colorless oil.

Aufarbeitung

  1. stirringAfter being further stirred at rt for 16 h
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (Mg2SO4)
  5. filtrationfiltered
  6. concentrationconcentration
  7. customThe residue was purified by silica gel column
  8. customto yield a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-3d3d0b07d9b84da49fe303d46f429500
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076345B2

Verknüpfte Notizen

Wird geladen…