Potassium Carbonate → 3-Chloro-5-[3-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyridin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl]-benzonitrile

HRID 426162Notes

Reaction equation

HRID 426162 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([C:12]2[NH:13][C:14](=[O:22])[NH:15][C:16](=[O:21])[C:17]=2[CH:18]([CH3:20])[CH3:19])=[O:11])[CH:9]=1)[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].[I-].[Li+].Cl[CH2:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]([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:34]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([C:12]2[N:13]([CH2:32][C:33]3[CH:38]=[CH:37][N:36]=[C:35]([N:39]4[C:40](=[O:49])[C:41]5[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=5)[C:47]4=[O:48])[CH:34]=3)[C:14](=[O:22])[NH:15][C:16](=[O:21])[C:17]=2[CH:18]([CH3:20])[CH3:19])=[O:11])[CH:9]=1)[C:5]#[N:6]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 591846992-[4-(Chloromethyl)-2-pyridinyl]-1H-isoindole-1,3(2H)-dioneHCID 596868393-Chloro-5-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-benzonitrile

Product 1

HCID 591846563-Chloro-5-[3-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyridin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl]-benzonitrileYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-Chloro-5-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-benzonitrile (317 mgmg, 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-pyridin-2-yl)-isoindole-1,3-dione (272 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 (1:1); Rf˜0.3 fraction was collected.) to afford 160 mg (29%) 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 (1:1); Rf˜0.3 fraction was collected.)

Sources & evidence

ORD record
ord-b7b4d3f1f0e8436ca70b3dce010aa299
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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