Methanol → 4-chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 398225Notes

Reaction equation

HRID 398225 reaction equation
C1(S([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([Cl:19])[C:13]=3[CH:12]=[C:11]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=O)=O)C=CC=CC=1.CO.[OH-].[Na+]>C1COCC1>[Cl:19][C:18]1[C:13]2[CH:12]=[C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:10][C:14]=2[N:15]=[CH:16][N:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 224845527-Benzenesulfonyl-4-chloro6-phenyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 224844424-chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidineYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Method D was dissolved in 10 mL of THF and to this solution was added 5.0 mL of methanol and 1.0 g of NaOH. The reaction mixture was stirred for 15 min., concentrated in vacuo and partitioned between a saturated aqueous solution of ammonium chloride (NH4Cl) and ethyl acetate. The resulting aqueous layer was extracted twice with ethyl acetate. The ethylacetate layers were combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by silica-gel chromatography (1:5 ethyl- acetate/hexane) to obtain 0.59 g (76%) of the title compound as a pale yellow solid, mp 145° C. (dec). LRMS: 230, 232 (M+2).

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between a saturated aqueous solution of ammonium chloride (NH4Cl) and ethyl acetate
  3. extractionThe resulting aqueous layer was extracted twice with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica-gel chromatography (1:5 ethyl- acetate/hexane)

Sources & evidence

ORD record
ord-fea806bc400246cbace104dbb2a59874
Source dataset
uspto-grants-2003_08
Patent number
US06610847B2

Reaction notes

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