Dimethylformamide → HCID 59184751, compound

HRID 426148Notes

Reaction equation

HRID 426148 reaction equation
[CH:1]([C:4]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:5]=1OC1C=C(C=C(C)C=1)C#N)([CH3:3])[CH3:2].[C:22](=[O:25])([O-])[O-].[K+].[K+].[I-].[Li+].Cl[CH2:31][C:32]1[CH:37]=[C:36]([CH3:38])[N:35]=[C:34]([N:39]2[C:47](=[O:48])[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40]2=[O:49])[CH:33]=1.C[N:51]([CH:53]=O)C>>[O:49]=[C:40]1[C:41]2[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:47](=[O:48])[N:39]1[C:34]1[CH:33]=[C:32]([CH2:31][N:6]2[C:5]([C:22]([C:45]3[CH:44]=[C:43]([CH:42]=[C:41]([CH3:40])[CH:46]=3)[C:53]#[N:51])=[O:25])=[C:4]([CH:1]([CH3:2])[CH3:3])[C:9](=[O:10])[NH:8][C:7]2=[O:11])[CH:37]=[C:36]([CH3:38])[N:35]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 59184674HCID 59184674, compoundHCID 596868373-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzonitrile

Product 1

HCID 59184751HCID 59184751, compoundYield 45%

Procedure

To a stirred solution of (73) (297 mg, 1 mmol), anhydrous powdered potassium carbonate (134 mg, 1 mmol), and lithium iodide (134 mg, 1 mmol) in DMF (5 ml) at room temperature, was added 2-(4-Chloromethyl-6-methyl-pyridin-2-yl)-isoindole-1,3-dione (286 mg, 1 mmol). After stirring for overnight, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (2:1); Rf˜0.2 fraction was collected.) to afford 250 mg (45%) of a white solid.

Workup

  1. customthe mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent, EA:hexanes (2:1); Rf˜0.2 fraction was collected.)

Sources & evidence

ORD record
ord-d121951e02d1495c9c71b3e03b2b1da8
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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