Sodium Thiosulfate → (2-fluoro-3-nitro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

HRID 1690030Notes

Reaction equation

HRID 1690030 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:11]([C:13]1[C:21]2[CH:20]=[N:19][CH:18]=[N:17][C:16]=2[NH:15][CH:14]=1)[OH:12].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C.O.O1CCCC1>[F:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11]([C:13]1[C:21]2[CH:20]=[N:19][CH:18]=[N:17][C:16]=2[NH:15][CH:14]=1)=[O:12]

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57963247(2-fluoro-3-nitro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol

Product 1

HCID 57963249(2-fluoro-3-nitro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanoneYield 83.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To (2-fluoro-3-nitro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol (37, 0.699 g, 2.42 mmol), 52 mL of tetrahydrofuran was added, followed by sodium bicarbonate (2.04 g, 24.2 mmol) and Dess-Martin periodinane (1.03 g, 2.42 mmol). The reaction was allowed to stir at room temperature for 30 minutes and 25 mL of saturated sodium thiosulfate and 30 mL of water were added, followed by 50 mL of ethyl acetate. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with a gradient of 20-80% ethyl acetate in hexanes (with 4% acetic acid). Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (38, 581 mg). MS (ESI) [M+H+]+=287.2.

Workup

  1. dry with materialThe organic layer was dried with magnesium sulfate
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe resulting material was purified by silica gel column chromatography
  5. washeluting with a gradient of 20-80% ethyl acetate in hexanes (with 4% acetic acid)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-22f9639a2168401db40b2cd595877665
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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