Dimethylformamide → 6-(1-Ethoxyvinyl)-1,2,4-triazin-3-amine
Reaction equation
Br[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[N:4][CH:3]=1.C(N([CH2:16][CH3:17])C(C)C)(C)C.[Cl-].[Li+].C([Sn](CC[CH2:33][CH3:34])(CCCC)CCCC)=C.CN(C)C=[O:38]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:33]([O:38][C:16]([C:2]1[N:7]=[N:6][C:5]([NH2:8])=[N:4][CH:3]=1)=[CH2:17])[CH3:34]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
A solution of 6-bromo-1,2,4-triazin-3-amine (780 mg, 4.46 mmol) in N,N-dimethylformamide (50 mL) was treated with tetrakis(triphenylphosphine) palladium (0) (258 mg, 0.22 mmol), N,N-diisopropylethyl amine (2284 mg, 11.14 mmol), lithium chloride (661 mg, 15.6 mmol), and vinyltri-n-butyltin (2093 mg, 5.79 mmol), and the reaction was heated at 120° C. for 2 h. The reaction mixture was cooled to room temperature and concentrated the solvent in vacuo. The residue was diluted with dichloromethane and washed with aqueous KF solution. The crude product was purified by flash chromatography in silica gel eluting with a ethyl acetate/hexane gradient to afford 380 mg (51%) of the title compound as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ ppm 8.48 (s, 1H), 5.41-5.39 (m, 3H), 4.36 (s, 1H), 3.98 (q, 2H), 1.43 (t, 2H).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated the solvent in vacuo
- additionThe residue was diluted with dichloromethane
- washwashed with aqueous KF solution
- customThe crude product was purified by flash chromatography in silica gel eluting with a ethyl acetate/hexane gradient
Sources & evidence
- ORD record
- ord-86b8d4173d8c41108c612bc462f0ffdb
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507676B2
Reaction notes
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