Cesium carbonate → HCID 118023250, compound

HRID 1486537Notes

Reaction equation

HRID 1486537 reaction equation
[CH3:1][C:2]1[C:3](=[O:16])[NH:4][C:5](=[O:15])[N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:24][CH:25]1[CH2:27][CH2:26]1>CC#N.CCOC(C)=O>[CH:25]1([CH2:24][N:4]2[C:3](=[O:16])[C:2]([CH3:1])=[CH:7][N:6]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[C:5]2=[O:15])[CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 15497670HCID 15497670, compound

Product 1

HCID 118023250HCID 118023250, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl 5-methyl-2,4-dioxo-pyrimidine-1-carboxylate (0.10 g, 0.44 mmol) was dissolved in dry MeCN (2.2 mL) and cesium carbonate was added (0.22 g, 0.66 mmol), followed by (bromomethyl)cyclopropane (0.13 mL, 1.33 mmol). The reaction mixture was stirred under nitrogen atmosphere at room temperature for 18 hrs. The reaction was then diluted with EtOAc and saturated aqueous NH4CI solution was added. The aqueous layer was extracted with EtOAc (3×15 mL), the combined organic phases were washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The crude was purified by column chromatography using a Teledyne ISCO apparatus (petroleum ether:EtOAc 80:20) to afford the title compound (0.09 g, 72%) as white solid. 1H NMR (400 MHz, CDCl3) δ 0.38-0.43 (m, 2H), 0.43-0.50 (m, 2H), 1.21-1.32 (m, 1H), 1.61 (s, 9H), 1.97 (s, 3H), 3.84 (d, J=7.2 Hz, 2H), 7.64 (s, 1H). MS (ESI) m/z: 303 [M-Na]−.

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extracted with EtOAc (3×15 mL)
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed under reduced pressure
  6. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-abe4f02d60884682a3dd27459c0bcf47
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

Loading…