Tetrahydrofuran → 1-phenyl-2-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethane-1,2-dione

HRID 1677403Notes

Reaction equation

HRID 1677403 reaction equation
[C:1]1([C:7](=[O:40])[CH2:8][C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)[N:16]=3)[N:11](S(C3C=CC(C)=CC=3)(=O)=O)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C[O:44]CC1.[OH-].[K+]>CO>[C:1]1([C:7](=[O:40])[C:8]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[C:20]([O:28][CH3:29])[C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=4)[N:16]=3)[NH:11][CH:10]=2)=[O:44])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 595410061-phenyl-2-[5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanone

Product 1

HCID 442060411-phenyl-2-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethane-1,2-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

1-Phenyl-2-[5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanone (100 mg, 0.18 mmol) was suspended in 4 ml of a 1:1 mixture of THF and methanol and 5N potassium hydroxide (0.180 ml, 0.9 mmol) was added dropwise. The reaction was heated at 40° C. for 2 hours. The solvents were evaporated using a rotary evaporator. Ethyl acetate and 1M hydrochloric acid were added to the residue and the layers were separated. The organic layer was washed with water, dried and concentrated. The crude reaction mixture was purified by preparative thin layer chromatography (50% ethyl acetate in hexanes) and flash chromatography to yield 4 mg of 1-phenyl-2-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethane-1,2-dione. MS: (M+H)+=418.

Workup

  1. additionwas added dropwise
  2. customThe solvents were evaporated
  3. customa rotary evaporator
  4. additionEthyl acetate and 1M hydrochloric acid were added to the residue
  5. customthe layers were separated
  6. washThe organic layer was washed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe crude reaction mixture
  10. customwas purified by preparative thin layer chromatography (50% ethyl acetate in hexanes) and flash chromatography

Sources & evidence

ORD record
ord-7f1800cf426e4888ada5ae3946e40367
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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