Potassium Carbonate → HCID 59686845, compound

HRID 426111Notes

Reaction equation

HRID 426111 reaction equation
[Br: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].Cl[CH2:23][C:24]1[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([N:31]2[C:39](=[O:40])[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]2=[O:41])[CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Li+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH3:21])[CH:20]=1)[C:5]([C:7]1[N:12]([CH2:23][C:24]2[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([N:31]3[C:39](=[O:40])[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:32]3=[O:41])[CH:25]=2)[C:11](=[O:13])[NH:10][C:9](=[O:14])[C:8]=1[CH:15]([CH3:16])[CH3:17])=[O:6]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 577518946-(3-bromo-5-methylbenzoyl)-5-isopropylpyrimidine-2,4(1H,3H)-dioneHCID 59184674HCID 59184674, compound

Product 1

HCID 59686845HCID 59686845, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (28) (351 mg, 1 mmol), (30) (287 mg, 1 mmol), anhydrous powdered potassium carbonate (138 mg, 1 mmol), and lithium iodide (134 mg, 1 mmol), was added DMF (5 ml). The mixture was stirred for overnight at room temperature. The mixture was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA: hexanes (from 1:2 to 1:1)) to afford 211 mg (35%) of a white solid; 1H NMR (200 MHz, CDCl3) δ 1.13 (3H, d, J=7.2 Hz), 1.20 (3H, d, J=7.2 Hz), 2.17-2.40 (4H, m), 2.47 (3H, s), 4.49 (1H, d, J=16.0 Hz), 5.15 (1H, d, J=16.0 Hz), 6.84 (1H, s), 6.91 (1H, s), 7.36 (1H, s), 7.53 (1H, s), 7.61 (1H, s), 7.77-7.96 (4H, m), 9.30 (1H, s).

Workup

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

Sources & evidence

ORD record
ord-1bf414a94066419097343c9bbe373d44
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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