Potassium Hydroxide → HCID 9901202, compound

HRID 854377Notes

Reaction equation

HRID 854377 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)[N:14]([CH3:23])[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)[N:14]([CH3:23])[CH:13]=3)[NH:9][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69431059HCID 69431059, compound

Product 1

HCID 9901202HCID 9901202, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-methoxy-6-(5-methoxy-1-methyl-1H-indol-3-yl)-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine [361 mg, Reference Example 4] in methanol (20 mL) was treated with potassium hydroxide (1.53 g). The reaction mixture was stirred for 16 hours at room temperature and refluxed 1 hour. The solution was evaporated under reduced pressure and the residue partitioned between water and ethyl acetate. The organic phase was separated, then dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with diethyl ether to give 4-methoxy-6-(5-methoxy-1-methyl-1H-indol-3-yl)-7H-pyrrolo[2,3-d]pyrimidine (155 mg) as a solid m.p.=184° C. MS: 309 [MH]+.

Workup

  1. temperaturerefluxed 1 hour
  2. customThe solution was evaporated under reduced pressure
  3. customthe residue partitioned between water and ethyl acetate
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-663467be7bf24b158da6da5a194695d4
Source dataset
uspto-grants-2007_08
Patent number
US07259154B2

Reaction notes

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