Sodium Carbonate → HCID 18507566, compound

HRID 1355817Notes

Reaction equation

HRID 1355817 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](OS(C(F)(F)F)(=O)=O)[C:5]([C:16]#[N:17])=[C:4]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1.[CH:23]([Sn](CCCC)(CCCC)CCCC)=[CH2:24].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[NH2:1][C:2]1[N:3]=[C:4]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[C:5]([C:16]#[N:17])=[C:6]([CH:23]=[CH2:24])[N:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 81998TributylvinyltinHCID 86583747Trifluoromethanesulfonic acid 2-amino-5-cyano-6-furan-2-yl-pyrimidin-4-yl ester

Product 1

HCID 18507566HCID 18507566, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 250 mg (0.75 mmol) trifluoromethanesulfonic acid 2-amino-5-cyano-6-furan-2-yl-pyrimidin-4-yl ester in 15 ml dioxane under argon at room temperature were added 0.22 ml (0.75 mmol) vinyltributylstannane, 86 mg (0.07 mmol) tetrakis(triphenyl-phosphine)palladium(O) and 1.5 ml (3.0 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 6 mg (4%) 2-amino-4-furan-2-yl-6-vinyl-pyrimidine-5-carbonitrile as a white crystalline solid. ES-MS m/e (%): 213 (M+H+, 100). Also obtained (as a by-product) was 3 mg (2%) 2-amino-4-ethyl-6-furan-2-yl-pyrimidine-5-carbonitrile as a yellow crystalline solid. ES-MS m/e (%): 215 (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-09b9694b101e4526a3e94cf7214276df
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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