Butyl vinyl ether → HCID 86641179, compound
Reaction equation
[CH:1]([O:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH2:2].[Cl:8][C:9]1[N:14]=[C:13](Cl)[C:12]([CH3:16])=[CH:11][N:10]=1.C(N(CC)CC)C>C(O[Pd]OC(=O)C)(=O)C>[CH2:4]([O:3]/[CH:1]=[CH:2]/[C:13]1[C:12]([CH3:16])=[CH:11][N:10]=[C:9]([Cl:8])[N:14]=1)[CH2:5][CH2:6][CH3:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Diacetoxypalladium (0.482 g, 2.15 mmol) was added in one portion to a mixture of 1-(vinyloxy)butane (11.91 mL, 92.02 mmol), 2,4-dichloro-5-methylpyrimidine (5 g, 30.67 mmol) and triethylamine (4.51 mL, 32.21 mmol) in degassed polyethylene glycol 200 (25 mL) under N2. The resulting mixture was stirred at 80° C. for 18 h. The mixture was then cooled and extracted with diethyl ether (3×75 mL). The combined organic solutions were dried (MgSO4), diluted with heptane (115 mL) and filtered through a 75 g silica plug, eluting with 2:1 diethyl ether/heptanes, to give the title compound (8.62 g, 124%) as a yellow oil which was used without further purification; 1H NMR: 0.92 (3H, t), 1.35-1.43 (2H, m), 1.60-1.71 (2H, m), 2.17 (3H, d), 4.06 (2H, t), 5.93 (1H, d), 7.90 (1H, d), 8.33 (1H, d); m/z: ES+ MH+ 226.
Workup
- temperatureThe mixture was then cooled
- extractionextracted with diethyl ether (3×75 mL)
- dry with materialThe combined organic solutions were dried (MgSO4)
- additiondiluted with heptane (115 mL)
- filtrationfiltered through a 75 g silica plug
- washeluting with 2:1 diethyl ether/heptanes
Sources & evidence
- ORD record
- ord-6e05044e0e664b3ca148836a057bb203
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946235B2
Reaction notes
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