Tetrahydrofuran → HCID 66602648, compound

HRID 2097537Notes

Reaction equation

HRID 2097537 reaction equation
O1CCCC1.[CH:6]1([CH2:9][OH:10])[CH2:8][CH2:7]1.[H-].[Na+].[Br:13][C:14]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:17]2[CH:18]=[N:19][NH:20][C:21](=[O:22])[C:16]=2[C:15]=1[CH2:32]Br>O>[Br:13][C:14]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:17]2[CH:18]=[N:19][NH:20][C:21](=[O:22])[C:16]=2[C:15]=1[CH2:32][O:10][CH2:9][CH:6]1[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 66602907HCID 66602907, compound

Product 1

HCID 66602648HCID 66602648, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10 ml of dehydrated tetrahydrofuran solution containing 0.92 g (13 mmol) of cyclopropylmethanol was added 0.25 g (6.2 mmol) of sodium hydride (60% dispersed material in mineral oil) under ice-cooling, the mixture was stirred at room temperature for 30 minutes, then, 10 ml of dehydrated tetrahydrofuran solution containing 0.56 g (1.3 mmol) of 2-bromo-3-bromomethyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 24-(f) was further added to the mixture, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=2:3 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 157 mg of the title compound as a pale yellowish solid. (Yield: 29%)

Workup

  1. temperaturecooling
  2. additionwas further added to the mixture
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. additionwas added to the reaction mixture
  5. extractionthe mixture was extracted with ethyl acetate
  6. customThe organic layer after separation
  7. washwas washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. additionthe fractions containing the desired compound
  11. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-007929f8109249cfbaf01bfa3cb30f24
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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