Sodium Bicarbonate → 3-(2-Bromo-1-hydroxyethyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097546Notes

Reaction equation

HRID 2097546 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=[CH:9][C:8]=2[N:7]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:6]=1)=[O:4].[BH4-].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[Br:1][CH2:2][CH:3]([C:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:20])[CH3:21])[N:10]=[CH:9][C:8]=2[N:7]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:6]=1)[OH:4]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 866270563-(2-Bromoacetyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 666029593-(2-Bromo-1-hydroxyethyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 150 ml of dehydrated tetrahydrofuran solution containing 6.64 g (12.9 mmol) of 3-(2-bromoacetyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 57-(b) was added dropwise 100 ml of tetrahydrofuran solution containing 486 mg (12.8 mmol) of sodium borohydride under cooling in ice-bath. After dropwise addition, the mixture was stirred at the same temperature for 2 hours. After completion of the reaction, to the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The organic layer 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=7:3 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 5.67 g of the title compound as a white solid. (Yield: 85%)

Workup

  1. temperatureunder cooling in ice-bath
  2. additionAfter dropwise addition
  3. customAfter completion of the reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionthe fractions containing the desired compound
  9. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-58871918b07749f5bf9504245d27093c
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

Loading…