Cyclohexanecarboxaldehyde → HCID 71258211, compound

HRID 1506112Notes

Reaction equation

HRID 1506112 reaction equation
C([Li])CCC.I[C:7]1[C:8]2[CH:15]=[CH:14][N:13]([Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[C:9]=2[N:10]=[CH:11][N:12]=1.[CH:26]1([CH:32]=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[Cl-].[NH4+]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH:26]1([CH:32]([C:7]2[C:8]3[CH:15]=[CH:14][N:13]([Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[C:9]=3[N:10]=[CH:11][N:12]=2)[OH:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 16275CyclohexanecarboxaldehydeHCID 25517Ammonium ChlorideHCID 86726610HCID 86726610, compoundHCID 178418339Butyllithium

Product 1

HCID 71258211HCID 71258211, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.6 M solution in hexane, 0.23 mL, 0.380 mmol) was gradually added dropwise to 4-iodo-7-(triisopropylsilyl)-7H-pyrrolo[2,3-d]pyrimidine (126 mg, 0.310 mmol) in tetrahydrofuran (1.5 mL) cooled to −78° C., and the reaction mixture was stirred at −78° C. for 30 minutes. After addition of cyclohexanecarbaldehyde (42 μL, 0.35 mmol) in tetrahydrofuran (1.5 mL), the reaction mixture was gradually warmed from −78° C. to room temperature and stirred for one day. After addition of saturated aqueous ammonium chloride, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hi Flash column amino type manufactured by Yamazen Corporation: hexane/ethyl acetate=10/1→7/1→4/1 (v/v)) to give the title compound as a colorless oil (65.5 mg, yield 55%).

Workup

  1. temperaturethe reaction mixture was gradually warmed from −78° C. to room temperature
  2. stirringstirred for one day
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Hi Flash column amino type

Sources & evidence

ORD record
ord-eff67ca07da640178c5499091b74e0f5
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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