Tributylvinyltin → HCID 86732066, compound

HRID 2199850Notes

Reaction equation

HRID 2199850 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[C:12]([CH3:13])=[N:11][C:10]([CH3:14])=[N:9]2)[N:5]=[C:4]([CH3:15])[N:3]=1.[CH2:16]([Sn](CCCC)(CCCC)C=C)[CH2:17]CC>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:14][C:10]1[N:11]=[C:12]([CH3:13])[N:8]([C:6]2[CH:7]=[C:2]([CH:16]=[CH2:17])[N:3]=[C:4]([CH3:15])[N:5]=2)[N:9]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 624817454-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidine

Product 1

HCID 86732066HCID 86732066, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidine (1-2) (5.2 g, 23.2 mmol) in degassed toluene (200 mL) under nitrogen was added tetrakis(triphenylphosphine)palladium(O) (1.3 g, 1.16 mmol) followed by tributyl(vinyl)tin (8.8 mL, 30.2 mmol) and the reaction was heated at 110° C. for 3 h. The solvent was concentrated in vacuo and the crude residue was purified by silica gel column chromatography (0-50% EtOAc/hexanes) to afford 4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methyl-6-vinylpyrimidine (1-3) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.63 (s, 1H), 6.76 (dd, 1H, J=17.3, 10.6 Hz), 6.52 (br d, 1H, J=17.3 Hz), 5.72 (br d, 1H, J=10.6 Hz), 2.91 (s, 3H), 2.72 (s, 3H), 2.42 (s, 3H). MS m/z=216 (M+H).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe crude residue was purified by silica gel column chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8b19ab2c3091493180707135fd64e0aa
Source dataset
uspto-grants-2016_06
Patent number
US09359348B2

Reaction notes

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