Sodium hydride → HCID 86685408, compound

HRID 570751Notes

Reaction equation

HRID 570751 reaction equation
[S:1]=[C:2]1[NH:7][C:6]2=[CH:8][S:9][CH:10]=[C:5]2[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[CH:14][CH:13]=1.[H-].[Na+].[C:26]([O:30][C:31](=[O:36])[NH:32][CH2:33][CH2:34]Br)([CH3:29])([CH3:28])[CH3:27].[Cl-].[NH4+]>CN(C)C=O>[O:11]=[C:4]1[N:3]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]([F:22])([F:23])[F:21])=[CH:16][CH:17]=2)[C:2]([S:1][CH2:34][CH2:33][NH:32][C:31](=[O:36])[O:30][C:26]([CH3:29])([CH3:28])[CH3:27])=[N:7][C:6]2=[CH:8][S:9][CH:10]=[C:5]12

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 86685406HCID 86685406, compound

Product 1

HCID 86685408HCID 86685408, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydrothieno[3,4-d]pyrimidin-4(1H)-one (1.59 g) was dissolved in N,N-dimethylformamide (20 ml), sodium hydride (60% in oil, 0.25 g) and tert-butyl(2-bromoethyl)carbamate (1.49 g) were added successively thereto under ice-cooling, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was poured into saturated aqueous ammonium chloride solution (30 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (2.12 g) as a white solid.

Workup

  1. temperatureunder ice-cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-27e42f2c43aa42109488cf5f8e66f94c
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

Loading…