Potassium Hydroxide → HCID 9835760, compound

HRID 854378Notes

Reaction equation

HRID 854378 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[CH:11]=[C:10]([C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=4)[NH:14][CH:13]=3)[N:9](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]=2[N:6]=[CH:7][N:8]=1.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[C:4]2[CH:11]=[C:10]([C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=4)[NH:14][CH:13]=3)[NH:9][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69429466HCID 69429466, compound

Product 1

HCID 9835760HCID 9835760, compoundYield 108.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-methoxy-6-(5-methoxy-1H-indol-3-yl)-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine [448 mg, Reference Example 5] in methanol (15 mL) was treated with potassium hydroxide (1.96 g). The reaction mixture was stirred for 2 hours at room temperature and the solvent was evaporated under reduced pressure. The residue was partitioned between water and ethyl acetate. The organic phase was separated, then dried over magnesium sulfate and then evaporated under reduced pressure. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (80:20, v/v) to give 4-methoxy-6-(5-methoxy-1H-indol-3-yl)-7H-pyrrolo[2,3-d]pyrimidine (320 mg) as a yellow solid m.p. >260° C. MS: 295 [MH]+.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was partitioned between water and ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (80:20, v/v)

Sources & evidence

ORD record
ord-02b2184d8cb54f458d194b702c9db0b1
Source dataset
uspto-grants-2007_08
Patent number
US07259154B2

Reaction notes

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