1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(1-Azidoethyl)-2-methylpyrimidine
Reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8](O)[CH3:9])=[CH:4][N:3]=1.C1C=CC(OP(OC2C=CC=CC=2)([N:20]=[N+:21]=[N-:22])=O)=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.CCOC(C)=O>[N:20]([CH:8]([C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[N:7][CH:6]=1)[CH3:9])=[N+:21]=[N-:22]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a stirred mixture of 1-(2-methylpyrimidin-5-yl)ethanol (2.48 g, 17 mmol) and diphenylphosphonic azide (9.3 mL, 41 mmol) in toluene (54.5 mL) at 0° C. was added neat 1,8-diazabicyclo[5.4.0]undec-7-ene (6.2 mL, 41 mmol). The reaction mixture was stirred at 0° C. for 30 minutes and then stirred at room temperature overnight. The mixture was diluted with EtOAc (100 mL) and washed with water (100 mL×2). The orangic layer was concentrated in vacuo and purified by silica gel chromatography (0-100% EtOAc/hexane) to afford a colorless oil.
Workup
- stirringstirred at room temperature overnight
- washwashed with water (100 mL×2)
- concentrationThe orangic layer was concentrated in vacuo
- custompurified by silica gel chromatography (0-100% EtOAc/hexane)
- customto afford a colorless oil
Sources & evidence
- ORD record
- ord-643e64c4dd864f5a811b1dc935789a37
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08076345B2
Reaction notes
Loading…