Potassium Iodide → HCID 66732326, compound

HRID 1022497Notes

Reaction equation

HRID 1022497 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:9](=[O:20])[N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=1)[C:7]2=[O:32])(=[O:3])[CH3:2].[I-].[K+].[Cl-].[Li+].[Ga].[CH3:38][Si:39]([CH:42](Br)[C:43]#[CH:44])([CH3:41])[CH3:40]>C1COCC1>[CH3:31][O:30][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[O:28][CH3:29])[CH2:21][N:8]1[C:7](=[O:32])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([C:1]([OH:3])([CH3:2])[CH2:44][C:43]#[C:42][Si:39]([CH3:41])([CH3:40])[CH3:38])[CH:5]=2)[N:10]([CH:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[C:9]1=[O:20]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 433294Lithium ChlorideHCID 5360835GalliumHCID 14732337HCID 14732337, compoundHCID 497644036-acetyl-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione

Product 1

HCID 66732326HCID 66732326, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.1 g of 6-acetyl-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione, 0.057 g of potassium iodide, 0.01 g of lithium chloride, 0.019 g of gallium and 0.065 g of trimethylsilylpropargyl bromide in 1 ml of THF is refluxed for 2 hours and then left for 2 days at room temperature. The reaction mixture is filtered through Celite and evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/EtOAc mixture from (70/30, v/v) to give 0.112 g of the expected product.

Workup

  1. temperatureis refluxed for 2 hours
  2. filtrationThe reaction mixture is filtered through Celite
  3. customevaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel
  5. washeluting with a DCM/EtOAc mixture from (70/30, v/v)

Sources & evidence

ORD record
ord-f438dca7d00149e7a4f0e979f2cbd6e8
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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