Dichloromethane → HCID 73672882, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[B-](F)(F)(F)[CH:11]=[CH2:12].[K+].C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(O)CC>[Cl:1][C:2]1[N:7]=[C:6]([CH:11]=[CH2:12])[C:5]([F:9])=[CH:4][N:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 105 °C
Procedure
2,4-Dichloro-5-fluoropyrimidine (111 g, 661.47 mmol, 1.00 equiv., 99.5%), potassium trifluoro(vinyl)borate (98 g, 716.72 mmol, 1.08 equiv., 98%), TEA (67 g, 98%), 1-propanol (1100 mL), PdCl2(dppf).CH2Cl2 (27 g, 33.06 mmol, 0.05 equiv) were added into five 2000-mL pressure tank reactors which purged and maintained with an inert atmosphere of nitrogen. The resulting solution was stirred overnight at 105° C. The reaction mixture of five batches was combined and then cooled to room temperature with a water bath. The solid was filtered out. The filtrate was concentrated under reduced vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:20) to afford 2-chloro-4-ethenyl-5-fluoropyrimidin as a highly volatile yellow oil.
Workup
- custompurged
- temperaturemaintained with an inert atmosphere of nitrogen
- additionThe reaction mixture of five batches
- temperaturecooled to room temperature with a water bath
- filtrationThe solid was filtered out
- concentrationThe filtrate was concentrated under reduced vacuum
- washeluted with ethyl acetate/petroleum ether (1:20)
Sources & evidence
- ORD record
- ord-93d647ebc35e4cc58d0217d015fd9e2e
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242984B2
Reaction notes
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