2-t-Butyl-5-hydroxy-1,4,5,6-tetrahydropyrimidine → 2-t-Butyl-5-(aminomethyl)oxazoline

HRID 2082433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2082433
[C:1]([C:5]1[NH:6][CH2:7][CH:8]([OH:11])[CH2:9][N:10]=1)([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1>[C:1]([C:5]1[O:11][CH:8]([CH2:7][NH2:6])[CH2:9][N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

3

Edukt 1

HCID 110948792-t-Butyl-5-hydroxy-1,4,5,6-tetrahydropyrimidine

Produkt 1

HCID 103746732-t-Butyl-5-(aminomethyl)oxazolineAusbeute 459,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Solid 2-t-butyl-5-hydroxy-1,4,5,6-tetrahydropyrimidine (2.55 g, 1.63 mmol) was heated to reflux in 100 mL of toluene for 22 hours. The solution was cooled to 25° C. and the slurry was filtered to remove 0.91 g of unconverted tetrahydropyrimidine after drying. The toluene filtrate was evaporated to give 1.17 g of 2-t-butyl-5-(aminomethyl)oxazoline as an oil: 1H NMR (CDCl3) δ 4.5 (m, 1H), 3.8 (apparent dd, 1H), 3.5 (apparent dd, 1H), 2.8 (apparent dq, 2H), 1.2 ppm (s, 9H), 13C NMR {1H} (CDCl3) δ 173.3 (1 C), 80.1 (1 C), 56.4 (1 C), 45.3 (1 C), 32.5 (1 C), 27.1 ppm (3 C). The neat oil gradually solidifies over a number of days, even at 0° C., reverting back to the tetrahydropyrimidine.

Aufarbeitung

  1. filtrationthe slurry was filtered
  2. customto remove 0.91 g of unconverted tetrahydropyrimidine
  3. customafter drying
  4. customThe toluene filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-cfb80a88be3548909b4b3066bc0e8908
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05189166

Notizen zur Reaktion

Wird geladen…