Cesium fluoride → HCID 49763188, compound

HRID 1022498Notes

Reaction equation

HRID 1022498 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]([OH:27])([CH3:26])[CH2:19][C:20]#[C:21][Si](C)(C)C)[CH:14]=2)[N:9]([CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:8]1=[O:34].[F-].[Cs+]>CN(C=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]([OH:27])([CH3:26])[CH2:19][C:20]#[CH:21])[CH:14]=2)[N:9]([CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:8]1=[O:34]

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 667323263-(3,4-dimethoxybenzyl)-6-[1-hydroxy-1-methyl-4-(trimethylsilyl)but-3-yn-1-yl]-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

Product 1

HCID 49763188HCID 49763188, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 2724141Tetrabutylammonium FluorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.112 g of the compound obtained in Step 9.1, 0.031 g of caesium fluoride and 0.003 g of tetrabutylammonium fluoride in 5 ml of DMF is stirred overnight at room temperature. The resulting mixture is evaporated under reduced pressure. The residue is taken up in DCM. This solution is washed with water, and the organic phase is dried over MgSO4, filtered and evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with EtOAc to give 0.084 g of the expected product.

Workup

  1. customThe resulting mixture is evaporated under reduced pressure
  2. washThis solution is washed with water
  3. dry with materialthe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-022b03faca7d4903bbcdafb83c49e47b
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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