Acetaldehyde → HCID 57831003, compound

HRID 1642077Notes

Reaction equation

HRID 1642077 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]3([C:16]([CH3:19])([CH3:18])[CH3:17])[O:15][CH2:14][CH2:13][O:12]3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].C([Li])CCC.[CH:27](=[O:29])[CH3:28].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C.O>[C:16]([C:11]1([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([CH:27]([OH:29])[CH3:28])[N:3]=3)[NH:8][CH:9]=2)[O:15][CH2:14][CH2:13][O:12]1)([CH3:19])([CH3:18])[CH3:17]

Participants

9

Reactant 5

HCID 177AcetaldehydeHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 57830990HCID 57830990, compoundHCID 178418339Butyllithium

Product 1

HCID 57831003HCID 57831003, compoundYield 61.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-bromo-7-(2-tert-butyl-[1,3]dioxolan-2-yl)-5H-pyrrolo[2,3-b]pyrazine (0.2 g, 0.61 mmol) was dissolved in 6 ml tetrahydrofuran. Sodium hydride (49 mg, 1.22 mmol, 60% mineral oil dispersion) was added and the mixture stirred for 15 min. The mixture was cooled in a dry ice/acetone bath and butyl lithium (0.37 ml, 0.92 mmol, 2.5M hexanes solution) was added slowly. After 5 min, acetaldehyde (85 ul, 1.52 mmol) was added. After a further 1 hr, ammonium chloride solution was added, then water and ethyl acetate. The layers were separated and the aqueous layer was extracted once more with ethyl acetate. The combined ethyl acetate layers were washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration and evaporation the residue was purified by silica gel chromatography(methanol/dichloromethane) to give 109 mg (61%) of 1-[7-(2-tert-butyl-[1,3]dioxolan-2-yl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-ethanol. (M+H)+=292.

Workup

  1. temperatureThe mixture was cooled in a dry ice/acetone bath
  2. waitAfter 5 min
  3. waitAfter a further 1 hr
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted once more with ethyl acetate
  6. washThe combined ethyl acetate layers were washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationAfter filtration and evaporation the residue
  9. customwas purified by silica gel chromatography(methanol/dichloromethane)

Sources & evidence

ORD record
ord-3f979496d6f94c58aecae91b0cc3898b
Source dataset
uspto-grants-2012_02
Patent number
US08119636B2

Reaction notes

Loading…