2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2,4-Dichloro-6-(3-chloro-thiophen-2-yl)-pyrimidine
Reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[Li]CCCC.[Cl:12][C:13]1[N:18]=[C:17]([Cl:19])[CH:16]=[CH:15][N:14]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1COCC1.CCOCC>[Cl:12][C:13]1[N:18]=[C:17]([Cl:19])[CH:16]=[C:15]([C:3]2[S:4][CH:5]=[CH:6][C:2]=2[Cl:1])[N:14]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-chlorothiophene (384 mg, 3.0 mmol) in THF (6 mL) at −78° C. was added n-BuLi (1.6 M, 2 mL) and the resulting mixture stirred for 45 minutes. The resulting product was added to a solution of 2,4-dichloropyrimidine (430 mg, 2.9 mmol) in ether (10 mL) at −30° C. and the resulting mixture stirred for 30 minutes, then warmed up to 0° C. and stirred for another 30 minutes. DDQ (700 mg, 3 mmol) was added and the resulting mixture was stirred overnight, then filtered through Celite®. The filtrate was concentrated and the residue was purified by silica gel column (EtOAc/hexanes, 1:5) to yield a white solid.
Workup
- stirringthe resulting mixture stirred for 30 minutes
- stirringstirred for another 30 minutes
- stirringthe resulting mixture was stirred overnight
- filtrationfiltered through Celite®
- concentrationThe filtrate was concentrated
- customthe residue was purified by silica gel column (EtOAc/hexanes, 1:5)
- customto yield a white solid
Sources & evidence
- ORD record
- ord-27539537da2646b39a7265817ece70a2
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022209B2
Reaction notes
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