Potassium Carbonate → HCID 66705452, compound

HRID 426121Notes

Reaction equation

HRID 426121 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8]OS(C)(=O)=O)[CH:5]=[C:4]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:3]=1.[CH:24]([C:27]1[C:32](=[O:33])[NH:31][C:30](=[O:34])[NH:29][C:28]=1[O:35][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][C:45]#[N:46])[CH:39]=[C:40]([CH3:42])[CH:41]=1)([CH3:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+].[I-].[Li+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][N:29]2[C:28]([O:35][C:36]3[CH:37]=[C:38]([CH:43]=[CH:44][C:45]#[N:46])[CH:39]=[C:40]([CH3:42])[CH:41]=3)=[C:27]([CH:24]([CH3:26])[CH3:25])[C:32](=[O:33])[NH:31][C:30]2=[O:34])[CH:5]=[C:4]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 59184646Methanesulfonic acid 2-fluoro-6-(4-methoxy-benzylamino)-pyridin-4-ylmethyl esterHCID 667053313-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-phenyl]-acrylonitrile

Product 1

HCID 66705452HCID 66705452, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask containing Methanesulfonic acid 2-fluoro-6-(4-methoxy-benzylamino)-pyridin-4-ylmethyl ester (44) (1 mmol), 3-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-phenyl]-acrylonitrile (43) (311 mg, 1 mmol), anhydrous powdered potassium carbonate (138 mg, 1 mmol), lithium iodide (134 mg, 1 mmol) was added anhydrous DMF (5 ml) and stirred for overnight at room temperature. The mixture was evaporated in vacuo. The residue was dissolved in methanol-dichloromethane (1:9), filtered through celite pad, and the filtrate was evaporated in vacuo to give a pale yellow foam. The crude product was purified by silica gel column chromatography (eluent, EA:hexane (1:2); The fraction of Rf=0.19 was collected) to afford 255 mg (46%) of a white foam; 1H NMR (300 MHz, CDCl3) δ: 1.10 (6H, d, J=6.9 Hz), 2.32 (3H, s), 2.68 (1H, m), 3.79 (3H, s), 4.31 (2H, d, J=5.5 Hz), 4.73 (2H, s), 5.02 (1H, t, J=5.5 Hz), 5.81 (1H, d, J=16.6 Hz), 5.85 (1H, s), 5.98 (1H, s), 6.64 (2H, s), 6.86-6.89 (2H, m), 6.98 (1H, s), 7.20-7.24 (3H, m), 8.98 (1H, s).

Workup

  1. customThe mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in methanol-dichloromethane (1:9)
  3. filtrationfiltered through celite pad
  4. customthe filtrate was evaporated in vacuo
  5. customto give a pale yellow foam
  6. customThe crude product was purified by silica gel column chromatography (eluent, EA:hexane (1:2)
  7. customThe fraction of Rf=0.19 was collected)

Sources & evidence

ORD record
ord-5489cedd329a4eea9185f3c87ec8027b
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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