2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4,6-Dichloro-2-ethenylpyrimidine
Reaction equation
C([Li])=C.[Li]C[CH2:6][CH2:7][CH3:8].C([Sn](C=C)(C=C)C=C)=C.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[N:22]=C[N:20]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(OCC)C>[CH:7]([C:6]1[N:20]=[C:19]([Cl:18])[CH:24]=[C:23]([Cl:25])[N:22]=1)=[CH2:8]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Vinyl lithium (10 mmol; generated from the reaction of nBuLi with tetravinyltin in diethyl ether) was added to a solution of 4,6-dichloropyrimidine (1.49 g, 10 mmol) in diethyl ether (70 mL) under an argon atmosphere at −30° C. The reaction mixture was quenched with acetic acid (600 mL) and water (200 mL) after stirring for 60 min. DDQ (2.27 g, 10 mmol) was added and the reaction mixture was warmed to 0° C. and stirred for 2 hr. The brownish slurry was then washed three times with 1M NaOH, once with brine and dried over MgSO4. Filtration followed by removal of volatiles under reduced pressure afforded a dark brown tar from which 2-vinyl-4,6-dichloropyrimidine was isolated by flash chromatography (10% ethyl acetate in hexane).
Workup
- customThe reaction mixture was quenched with acetic acid (600 mL) and water (200 mL)
- stirringstirred for 2 hr
- washThe brownish slurry was then washed three times with 1M NaOH
- dry with materialonce with brine and dried over MgSO4
- filtrationFiltration
- customfollowed by removal of volatiles under reduced pressure
Sources & evidence
- ORD record
- ord-67c0756073e1490d89fdeeb67837a60e
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07037916B2
Reaction notes
Loading…