Tetrahydrofuran → HCID 66602614, compound

HRID 2097508Notes

Reaction equation

HRID 2097508 reaction equation
O1CCCC1.[CH:6]1([OH:10])[CH2:9][CH2:8][CH2:7]1.[H-].[Na+].[Br:13][C:14]1[N:31]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:17]2[CH:18]=[N:19][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:21](=[O:22])[C:16]=2[C:15]=1[CH2:40]Br>O>[Br:13][C:14]1[N:31]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:17]2[CH:18]=[N:19][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:21](=[O:22])[C:16]=2[C:15]=1[CH2:40][O:10][CH:6]1[CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 76218CyclobutanolHCID 66602679HCID 66602679, compound

Product 1

HCID 66602614HCID 66602614, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10 ml of dehydrated tetrahydrofuran solution containing 0.89 g (12 mmol) of cyclobutanol was added 0.25 g (6.2 mmol) of sodium hydride (60% dispersed material in mineral oil) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. To the mixture was further added 0.70 g (1.2 mmol) of 2-bromo-3-bromomethyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo-[2,3-d]pyridazin-4-one obtained in Reference example 25-(a), and the mixture was stirred at 45° C. for 1 hour. 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 concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=7:3 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 561 mg of the title compound as a pale yellowish oil. (Yield: 82%)

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 45° C. for 1 hour
  3. additionwas added to the reaction mixture
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe organic layer after separation
  6. washwas washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionthe fractions containing the desired compound
  10. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-9a42334644374663b56f33457459c625
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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