3-Furanol, tetrahydro- → HCID 86726519, compound

HRID 1487691Notes

Reaction equation

HRID 1487691 reaction equation
[H-].[Na+].[O:3]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4]1.[Cl:9][C:10]1[N:11]=[C:12](Cl)[C:13]2[C:18]([C:19]3[CH:28]=[CH:27][C:22]4[N:23]=[C:24]([CH3:26])[O:25][C:21]=4[CH:20]=3)=[CH:17][N:16]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:14]=2[N:15]=1>C1COCC1>[Cl:9][C:10]1[N:11]=[C:12]([O:8][CH:5]2[CH2:6][CH2:7][O:3][CH2:4]2)[C:13]2[C:18]([C:19]3[CH:28]=[CH:27][C:22]4[N:23]=[C:24]([CH3:26])[O:25][C:21]=4[CH:20]=3)=[CH:17][N:16]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:36])[CH3:35])[C:14]=2[N:15]=1

Participants

5

Reactant 3

HCID 99603-Furanol, tetrahydro-HCID 24758Sodium hydrideHCID 867264196-(2,4-Dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole

Product 1

HCID 86726519HCID 86726519, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (1.2 equiv, 60% by weight in mineral oil) in THF (0.3 M) under nitrogen atmosphere was added tetrahydrofuran-3-ol (1.5 equiv) in THF (0.6 M) at 0° C. The resulting reaction mixture was stirred at 0° C. for 20 min. A solution of 6-(2,4-dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole (1 equiv) in THF (0.6 M) was added and the resulting reaction mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (0.6 M) and the organic solvents were removed under reduced pressure. The resulting residue was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated under reduced pressure and the crude product was purified by silica gel chromatography (15% ethyl acetate in petroleum ether) to afford the title compound (83% yield). MS (ESI) m/z 501.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. customthe resulting reaction mixture
  3. stirringwas stirred at room temperature for 3 h
  4. customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution (0.6 M)
  5. customthe organic solvents were removed under reduced pressure
  6. additionThe resulting residue was diluted with water
  7. extractionextracted with ethyl acetate
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customThe filtrate was evaporated under reduced pressure
  12. customthe crude product was purified by silica gel chromatography (15% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-fd61bff9326d4a588888397a3667d587
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

Loading…