Reaktion #73096

Reaktionsgleichung

HCl

NaOCH3

pyrimidine-2-carbonitrile

Na2CO3

2,2-dimethoxyethanamine

→

2-(1H-imidazol-2-yl)pyrimidine

Lösungsmittel

MeOH

AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThis mixture was stirred for 1 h
2. 2
   TemperaturThe resulting acidic solution was heated
3. 3
   Temperaturat reflux for 18 h
4. 4
   TemperaturAfter cooling to rt
5. 5
   Extraktionextracted with EtOAc
6. 6
   Einengenthe organic layer was concentrated

Vorschrift

To a solution of NaOCH3 (270 mg) in 50 mL of MeOH, pyrimidine-2-carbonitrile (1-Im-3, 50 mmol) was added. The mixture was stirred at rt for 1 h, then 2,2-dimethoxyethanamine (50 mmol) was added followed by 2 mL of AcOH. This mixture was stirred for 1 h, then 6N HCl was added to adjust pH=1. The resulting acidic solution was heated at reflux for 18 h. After cooling to rt, the reaction was poured into a mixture of ice and aqueous Na2CO3 solution, then extracted with EtOAc and the organic layer was concentrated to give 2-(1H-imidazol-2-yl)pyrimidine (Imidazole 3). LCMS (0.01% Ammonia): 147.2 m/z (M+H)+; 1H-NMR (DMSO-d6, 500 MHz): δ: 13.04 (bs, 1H), 8.87 (d, 2H, J=5.0 Hz), 7.44 (t, 1H, J=5.0 Hz), 7.24 (s, 2H).

Quelle