Sodium Carbonate → HCID 18507439, compound

HRID 1355807Notes

Reaction equation

HRID 1355807 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]#[N:10])=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.[CH:17]([Sn](CCCC)(CCCC)CCCC)=[CH2:18].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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]>[NH2:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([C:9]#[N:10])=[C:6]([CH:17]=[CH2:18])[N:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 81998TributylvinyltinHCID 18507370HCID 18507370, compound

Product 1

HCID 18507439HCID 18507439, compoundYield 8.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 515 mg (2.23 mmol) 2-amino-4-chloro-6-phenyl-pyrimidine-5-carbonitrile in 20 ml dioxane under argon at room temperature were added 0.65 ml (2.23 mmol) vinyltributylstannane, 258 mg (0.22 mmol) tetrakis(triphenylphosphine)palladium(O) and 4.5 ml (9.0 mmol) 2M aqueous sodium carbonate solution. The reaction mixture was heated at reflux for 16 h, then concentrated in vacuo. The residue was partitioned between ethyl acetate and water and the organic phase washed with brine, dried over sodium sulfate, and concentrated in vacuo. Flash chromatography (1/1 ethyl acetate/hexane) followed by trituration in ether afforded 40 mg (8%) 2-Amino-4-phenyl-6-vinyl-pyrimidine-5-carbonitrile as a yellow crystalline solid. EI-MS m/e (%): 222 (M+, 85), 221 ([M—H]+, 100).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and water
  5. washthe organic phase washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-583ffc9b987e4ac58d168fecb0545d65
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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