Sodium Hydroxide → 4-chloro-6-(1-naphthyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 447685Notes

Reaction equation

HRID 447685 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][CH:12]=3)[N:8](S(C3C=CC=CC=3)(=O)=O)[C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 866187344-chloro-6-(1-naphthyl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 866187354-chloro-6-(1-naphthyl)-7H-pyrrolo[2,3-d]pyrimidineYield 69.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-chloro-6-(1-naphthyl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (350 mg, 0.73 mmol) in THF (2.50 mL) was added a solution of NaOH (205 mg, 5.13 mmol) in methanol (1.19 mL), and the mixture was stirred for 15 minutes. After quenching by addition of saturated NH4Cl solution (80.0 mL), the mixture was extracted with ethyl acetate (3×100 mL). The organic layers were combined, dried over MgSO4, filtered, and evaporated under vacuum. The residue was dissolved in a small amount of methanol, and the suspension was filtered through a glass pad filter. The white solid was dried under high to afford the title compound (141 mg, 65%).

Workup

  1. customAfter quenching by addition of saturated NH4Cl solution (80.0 mL)
  2. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. dissolutionThe residue was dissolved in a small amount of methanol
  7. filtrationthe suspension was filtered through a glass pad
  8. filtrationfilter
  9. customThe white solid was dried under high

Sources & evidence

ORD record
ord-b7a2d40dbf0d42e28b35770b6fef7001
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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