Pivalaldehyde → HCID 57831005, compound

HRID 1642071Notes

Reaction equation

HRID 1642071 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:10](I)=[CH:9][N:8]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])[C:5]2=[N:6][CH:7]=1.C([Mg]Cl)(C)C.[Cl-].[Li+].[CH3:29][C:30]([CH:33]=[O:34])([CH3:32])[CH3:31]>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]2[C:10]([CH:33]([OH:34])[C:30]([CH3:32])([CH3:31])[CH3:29])=[CH:9][N:8]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 12417PivalaldehydeHCID 433294Lithium ChlorideHCID 57830996HCID 57830996, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 57831005HCID 57831005, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2-Chloro-7-iodo-5-triisopropylsilanyl-5H-pyrrolo[2,3-b]pyrazine (0.56 g, 1.28 mmol) was dissolved in 10 mL of dry tetrahydrofuran and stirred under argon with cooling to −78° C. A solution of isopropylmagnesium chloride with lithium chloride (3 mL, 1M, 3 mmol) was added via syringe. After 10 m, neat pivaldehyde (0.325 mL, 3 mmol, distilled) was added all at once. After 1 h at −78° C., the reaction was quenched by the addition of saturated aqueous ammonium chloride, then diluted with ethyl acetate and allowed to warm to ambient temperature. The organic layer was then washed successively with saturated aqueous sodium bicarbonate and brine. After drying over magnesium sulfate, the solution was filtered and solvent removed, and carried directly into the next step.

Workup

  1. customthe reaction was quenched by the addition of saturated aqueous ammonium chloride
  2. additiondiluted with ethyl acetate
  3. temperatureto warm to ambient temperature
  4. washThe organic layer was then washed successively with saturated aqueous sodium bicarbonate and brine
  5. dry with materialAfter drying over magnesium sulfate
  6. filtrationthe solution was filtered
  7. customsolvent removed

Sources & evidence

ORD record
ord-b98187823657477fb961a75e19c0413f
Source dataset
uspto-grants-2012_02
Patent number
US08119636B2

Reaction notes

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