Hydrochloric Acid → HCID 70982842, compound

HRID 1506117Notes

Reaction equation

HRID 1506117 reaction equation
[CH:1]1([CH:7]([C:9]2[C:10]3[CH:17]=[CH:16][N:15]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:11]=3[N:12]=[CH:13][N:14]=2)[NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:26][Si](C)(C)CCOCN1C2N=CN=C(CN)C=2C=C1.Cl>COC(OC)N(C)C.C(OCC)(=O)C>[CH:1]1([C:7]2[N:8]=[CH:26][N:14]3[C:9]=2[C:10]2[CH:17]=[CH:16][N:15]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:11]=2[N:12]=[CH:13]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 71259846HCID 71259846, compoundHCID 86726611HCID 86726611, compound

Product 1

HCID 70982842HCID 70982842, compoundYield 302.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 78373Dimethylformamide dimethyl acetalSolvent2×

Procedure

Cyclohexyl(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)methanamine (10 mg. 0.028 mmol) in N,N-dimethylformamide dimethyl acetal (0.7 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 (1.0 mL) and stirred at 230° C. for 1.5 hours under microwave irradiation. Separately, cyclohexyl(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-ylmethanamine (89 mg, 0.25 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 (4.5 mL) and stirred at 230° C. for 1.5 hours under microwave irradiation. The reaction mixture and the previously obtained reaction mixture were combined, diluted with ethyl acetate, acidified with 1 M hydrochloric acid 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 residue was purified by silica gel thin layer chromatography (hexane/ethyl acetate=2/1→1/1→1/2 (v/v)) to give the title compound as a pale yellow oil (31.4 mg, yield 30%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in 1,3-dimethylimidazolidin-2-one (1.0 mL)
  3. temperatureto cool to room temperature
  4. concentrationconcentrated under reduced pressure
  5. dissolutionthe resulting residue was dissolved in 1,3-dimethylimidazolidin-2-one (4.5 mL)
  6. stirringstirred at 230° C. for 1.5 hours under microwave irradiation
  7. customThe reaction mixture and the previously obtained reaction mixture
  8. washwashed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  9. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel thin layer chromatography (hexane/ethyl acetate=2/1→1/1→1/2 (v/v))

Sources & evidence

ORD record
ord-f406665ea9774f52aa9a555b44426789
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

Loading…