Triphenylphosphine → HCID 59540949, compound

HRID 1677532Notes

Reaction equation

HRID 1677532 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:13]2[N:14]=[C:15]3[C:21]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:20][N:19]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:16]3=[N:17][CH:18]=2)[CH:5]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1.[CH3:36][S:37][CH2:38][CH2:39]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:25][C:23]([CH3:26])([CH3:24])[C:22]([C:21]1[C:15]2[C:16](=[N:17][CH:18]=[C:13]([C:4]3[CH:5]=[C:6]([N:8]4[CH2:12][CH2:11][CH2:10][CH2:9]4)[CH:7]=[C:2]([O:1][CH2:39][CH2:38][S:37][CH3:36])[CH:3]=3)[N:14]=2)[N:19]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:20]=1)=[O:27]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 789252-(Methylthio)ethanol3×HCID 59540752HCID 59540752, compound

Product 1

HCID 59540949HCID 59540949, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flask was charged with 1-[2-(3-hydroxy-5-pyrrolidin-1-yl-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (140 mg, 0.28 mmol), 2-methylsulfanyl-ethanol (reagent A, 0.03 ml, 0.34 mmol), triphenylphosphine (reagent B, 89 mg, 0.34 mmol). THF (1.5 ml) was added and the mixture cooled (ice bath) under nitrogen atmosphere. Diisopropyl azodicarboxylate (reagent C, 0.07 ml, 0.34 mmol) was added via syringe and the material was warmed to ambient. After 1 hour a further 1.2 equivalents each of reagents A, B and C were added. After 2 hours repeat. The mixture was stirred overnight. The crude was loaded onto 2 preparative TLC plates eluting with 20% EtOAc in hexanes. The product band was collected providing 2,2-dimethyl-1-[2-[3-(2-methylsulfanyl-ethoxy)-5-pyrrolidin-1-yl-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one, 82 mg as a yellow viscous oil.

Workup

  1. temperaturethe mixture cooled (ice bath) under nitrogen atmosphere
  2. temperaturethe material was warmed to ambient
  3. washeluting with 20% EtOAc in hexanes
  4. customThe product band was collected

Sources & evidence

ORD record
ord-cb59dea83ee247019b445e4e67ef26ee
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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