HCID 67164558, compound → HCID 21725232, compound

HRID 552748Notes

Reaction equation

HRID 552748 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[O:12][C@@H:11]([N:23]2[C:27]3[N:28]=[CH:29][N:30]=[C:31]([NH:32][C:33](=[O:40])[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:26]=3[CH:25]=[CH:24]2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C1COCC1.N1C=CC=CC=1.N1C=CC=CC=1>[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][OH:15])[O:12][C@@H:11]([N:23]2[C:27]3[N:28]=[CH:29][N:30]=[C:31]([NH:32][C:33](=[O:40])[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:26]=3[CH:25]=[CH:24]2)[CH2:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67164558HCID 67164558, compound

Product 1

HCID 21725232HCID 21725232, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 16069498Pyridine tetrahydrofuranSolvent

Procedure

To a solution of N-{7-[(2R,4S,5R)-4-{[tert-butyl(dimethyl)silyl]oxy}-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}benzamide (1.06 g, 1.82 mmol) in 18 mL THF/pyridine (1:1) was added approximately 20 drops of hydrofluoridic acid in pyridine. The mixture was stirred at r.t. for 30 h. The reaction was quenched by slowly adding to saturated aq NaHCO3 (100 mL) and the solution was extracted with EtOAc (3×50 mL). The combined organics were washed with saturated aq Cu(SO4)2 (50 mL) and saturated aq EDTA.Na2. The combined organics were dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography (15 to 50% EtOAc/hexanes) to isolate the title compound as a white foam (0.264 g, 31%).

Workup

  1. customThe reaction was quenched
  2. additionby slowly adding to saturated aq NaHCO3 (100 mL)
  3. extractionthe solution was extracted with EtOAc (3×50 mL)
  4. washThe combined organics were washed with saturated aq Cu(SO4)2 (50 mL) and saturated aq EDTA
  5. dry with materialThe combined organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (15 to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f85c3a370a5242b8a672625f5b023515
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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