HCID 45084195, compound → (1-methyl-cyclopropyl)-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

HRID 1677390Notes

Reaction equation

HRID 1677390 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[N:9]=2)[N:4]([Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[CH:3]=1.[Li]CCCC.CON(C)[C:41]([C:43]1([CH3:46])[CH2:45][CH2:44]1)=[O:42]>O1CCCC1>[CH3:46][C:43]1([C:41]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=4)[N:9]=3)[N:4]([Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[CH:3]=2)=[O:42])[CH2:45][CH2:44]1

Participants

5

Reactant 3

HCID 45084195HCID 45084195, compoundHCID 595405257-iodo-5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazineHCID 178418339Butyllithium

Product 1

HCID 67342981(1-methyl-cyclopropyl)-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanoneYield 19.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-iodo-5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine (116 mg, 0.2 mmol) in anhydrous tetrahydrofuran (3 ml) was cooled to −78° C. and treated with nBuLi (2.13M in hexanes, 0.13 ml, 0.27 mmol) dropwise. The solution was stirred for 30 seconds and 1-methyl-cyclopropanecarboxylic acid methoxy-methyl-amide (88 mg, 0.61 mmol) was added in one portion. The reaction mixture was stirred at −78° C. for 30 minutes. The reaction mixture was quenched with saturated aqueous NaHSO4 and then partitioned between EtOAc/brine. The organic layers were collected, dried over MgSO4, filtered, and concentrated giving a yellow oil. The oil was purified by silica gel chromatography using 2-30% EtOAc in hexanes as eluant to provide 20 mg (19%) of (1-methyl-cyclopropyl)-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 30 minutes
  2. customThe reaction mixture was quenched with saturated aqueous NaHSO4
  3. custompartitioned between EtOAc/brine
  4. customThe organic layers were collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customgiving a yellow oil
  9. customThe oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0062310e0b884a4fb4055927ab0f1e23
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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