Sodium borohydride → HCID 86610858, compound

HRID 2105240Notes

Reaction equation

HRID 2105240 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH:10]=CC)[N:5]=[C:4]([N:13]2[CH2:17][CH2:16][CH2:15][CH:14]2[C:18]2[O:22][N:21]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH:19]=2)[N:3]=1.I([O-])(=O)(=O)=[O:30].[Na+].[BH4-].[Na+]>C(O)(C)(C)C.C1COCC1.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][OH:30])[N:5]=[C:4]([N:13]2[CH2:17][CH2:16][CH2:15][CH:14]2[C:18]2[O:22][N:21]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH:19]=2)[N:3]=1

Participants

9

Reactant 3

HCID 4311764Sodium borohydrideHCID 23667635Sodium periodateHCID 86610859HCID 86610859, compound

Product 1

HCID 86610858HCID 86610858, compoundYield 36%

Reagents, catalysts & solvents 5

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent4×HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.5% w/v osmium tetroxide in tert-butanol (0.47 ml) was added to a vigorously stirred solution of 4-chloro-6-(pent-3-en-1-yl)-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}pyrimidine (prepared as described in Example 34) in THF (10.5 ml) and water (2.8 ml). Solid sodium periodate (951 mg, 4.44 mmol) was then added. The reaction was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (Na2SO4), and the solvent removed by evaporation. The residue was dissolved in THF (13.5 ml) and distilled water (5.0 ml) and sodium borohydride (59 mg, 1.59 mmol) was added. The reaction was stirred at ambient temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and water and the layers partitioned and separated. The ethyl acetate layer was washed with water and saturated brine, dried (Na2SO4) and the solvent removed by evaporation. The residue was purified by flash chromatography on silica gel eluting with methanol/DCM (1.5:98.5) to give the title compound (205 mg, 36%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water and saturated brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed by evaporation
  5. dissolutionThe residue was dissolved in THF (13.5 ml)
  6. additionwas added
  7. stirringThe reaction was stirred at ambient temperature for 18 hours
  8. customthe layers partitioned
  9. customseparated
  10. washThe ethyl acetate layer was washed with water and saturated brine
  11. dry with materialdried (Na2SO4)
  12. customthe solvent removed by evaporation
  13. customThe residue was purified by flash chromatography on silica gel eluting with methanol/DCM (1.5:98.5)

Sources & evidence

ORD record
ord-79a82ffd5e31445aada11bce13eb51a4
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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