Potassium Carbonate → 2-{4-[6-(3,5-Dimethyl-benzoyl)-5-isopropyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl]-6-methyl-pyridin-2-yl}-isoindole-1,3-dione

HRID 426151Notes

Reaction equation

HRID 426151 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH3:21])[CH:20]=1)[C:5]([C:7]1[NH:12][C:11](=[O:13])[NH:10][C:9](=[O:14])[C:8]=1[CH:15]([CH3:17])[CH3:16])=[O:6].C(=O)([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>CN(C=O)C>[CH3:21][C:19]1[CH:18]=[C:4]([CH:3]=[C:2]([CH3:1])[CH:20]=1)[C:5]([C:7]1[N:12]([CH2:31][C:32]2[CH:37]=[C:36]([CH3:38])[N:35]=[C:34]([N:39]3[C:47](=[O:48])[C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[C:40]3=[O:49])[CH:33]=2)[C:11](=[O:13])[NH:10][C:9](=[O:14])[C:8]=1[CH:15]([CH3:17])[CH3:16])=[O:6]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 222565826-(3,5-Dimethyl-benzoyl)-5-isopropyl-1H-pyrimidine-2,4-dioneHCID 59184674HCID 59184674, compound

Product 1

HCID 591847902-{4-[6-(3,5-Dimethyl-benzoyl)-5-isopropyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl]-6-methyl-pyridin-2-yl}-isoindole-1,3-dioneYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (20) (286 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 (1:1)) to afford 273 mg (51%) of a white solid. m.p. 310-311° C.; 1H NMR (200 MHz, CDCl3) δ 1.14 (3H, d, J=6.9 Hz), 1.22 (3H, d, J=6.9 Hz), 2.27 (6H, s), 2.36 (1H, m), 2.43 (3H, s), 4.54 (1H, d, J=16.2 Hz), 5.04 (1H, d, J=16.2 Hz), 6.82 (1H, s), 6.94 (1H, s), 7.21 (1H, s), 7.39 (2H, s), 7.77-7.82 (2H, m), 7.91-7.95 (2H, m), 8.96 (1H, s).

Workup

  1. customthe mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:1))

Sources & evidence

ORD record
ord-a533cc0ed57a432e89fd325088d16a3b
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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