Potassium Fluoride → 2-Chloro-5-(1-ethoxyvinyl)pyrimidine
Reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:14]([O:16][CH2:17][CH3:18])=[CH2:15])CCC.[F-].[K+]>CN(C=O)C.CCOCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:8][C:5]1[N:4]=[CH:3][C:2]([C:14]([O:16][CH2:17][CH3:18])=[CH2:15])=[CH:7][N:6]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 5-bromo-2-chloropyrimidine (600 mg, 3.13 mmol) in dry DMF (10 mL) under N2 were added tributyl(1-ethoxyvinyl)stannane (1.09 mL, 3.23 mmol) and Pd(PPh3)2Cl2 (113 mg, 0.161 mmol). The mixture was stirred at 100° C. for 3 h and at rt for 16 h. The mixture was diluted with ether (20 mL), and treated with aqueous KF solution (5 g of KF in 3 mL of water). The mixture was stirred vigorously for 1 h at room temperature before being filtered through diatomaceous earth. The filtrate was washed with satd aq NaHCO3 and brine. The aqueous phase was extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated to give 2-chloro-5-(1-ethoxyvinyl)pyrimidine (350 mg, yield 61%).
Workup
- stirringThe mixture was stirred vigorously for 1 h at room temperature
- filtrationbefore being filtered through diatomaceous earth
- washThe filtrate was washed with satd aq NaHCO3 and brine
- extractionThe aqueous phase was extracted with EtOAc
- dry with materialThe combined organic layer was dried over anhydrous Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9f770e1a805d415e9f445a0480a3d4a4
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569292B2
Reaction notes
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