Dimethylformamide dimethyl acetal → HCID 71141839, compound

HRID 1506123Notes

Reaction equation

HRID 1506123 reaction equation
[NH2:1][CH:2]([C:19]1[C:20]2[CH:27]=[CH:26][N:25]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:21]=2[N:22]=[CH:23][N:24]=1)[CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4]1.[CH3:36]OC(OC)N(C)C>>[CH3:33][Si:32]([CH3:35])([CH3:34])[CH2:31][CH2:30][O:29][CH2:28][N:25]1[C:21]2[N:22]=[CH:23][N:24]3[CH:36]=[N:1][C:2]([CH:3]4[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]5[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=5)=[O:10])[CH2:4]4)=[C:19]3[C:20]=2[CH:27]=[CH:26]1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 71258485HCID 71258485, compound

Product 1

HCID 71141839HCID 71141839, compound

Procedure

Benzyl 3-[amino(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)methyl]piperidine-1-carboxylate (63 mg, 0.13 mmol) in N,N-dimethylformamide dimethyl acetal (1 mL) was stirred at 170° C. for 30 minutes under microwave irradiation. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure, and the resulting residue was dissolved in 1,3-dimethylimidazolidin-2-one (1 mL) and stirred at 230° C. for 1.5 hours under microwave irradiation. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate and washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel thin layer chromatography (hexane/ethyl acetate=1/1→1/2 (v/v)) to give a brown oil containing the title compound (45.2 mg). The resulting mixture was used for the next step.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in 1,3-dimethylimidazolidin-2-one (1 mL)
  3. temperatureto cool to room temperature
  4. additiondiluted with ethyl acetate
  5. washwashed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrate was purified by silica gel thin layer chromatography (hexane/ethyl acetate=1/1→1/2 (v/v))
  9. customto give a brown oil

Sources & evidence

ORD record
ord-61aaaf20e1a64623bbe135706c49718f
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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