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Sodium Hydroxide → 4-(5-fluoro-2-methoxyphenyl)-6-iodo-7H-pyrrolo[2,3-d]pyrimidine

HRID 528001
Notes
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Reaction equation

HRID 528001 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([I:17])[N:14](S(C4C=CC=CC=4)(=O)=O)[C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1.[OH-].[Na+]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([I:17])[NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 90417868HCID 90417868, compound

Product 1

HCID 904186604-(5-fluoro-2-methoxyphenyl)-6-iodo-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of Example 3C (3.5 g, 6.78 mmol) in 70 mL dioxane was treated with aqueous sodium hydroxide (11.30 mL, 67.8 mmol, 6 M) and stirred at 100° C. for 1 hour. The reaction mixture was cooled and diluted with 300 mL of water. The aqueous mixture was extracted with ethyl acetate (3×), and the combined organic fractions were washed with brine, dried over magnesium sulfate and concentrated to give the title compound. MS (ESI+) m/z 370.1 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe aqueous mixture was extracted with ethyl acetate (3×)
  3. washthe combined organic fractions were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f0ce5eff1bd046f9a62c99e198bd1d43
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346813B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes