Methyl iodide → (R)-tert-butyl methyl((1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methyl)carbamate

HRID 57609Notes

Reaction equation

HRID 57609 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][N:22]=3)[CH:17]=[C:16]([C:24]3[CH:29]=[CH:28][C:27]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[CH:26][CH:25]=3)[N:15]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:39]I>C1COCC1>[CH3:39][N:7]([CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][N:22]=3)[CH:17]=[C:16]([C:24]3[CH:29]=[CH:28][C:27]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[CH:26][CH:25]=3)[N:15]=2)[CH2:10]1)[C:6](=[O:36])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71113521(S)-tert-butyl(1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methylcarbamate

Product 1

HCID 71113509(R)-tert-butyl methyl((1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under N2, to a solution of (S)-tert-butyl(1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methylcarbamate (150 mg, 0.31 mmol) in anhydrous THF (10 mL) was slowly added sodium hydride (49 mg, 1.22 mmol) at 0° C. The mixture was warmed up and stirred at room temperature for 0.5 h. The reaction mixture was then cooled to 0° C., and CH3I (174 mg, 1.22 mmol) was added slowly. After the completion of the addition, the reaction mixture was stirred at reflux for 4 hours, cooled to ambient temperature, quenched with H2O, and extracted with EtOAc. The combined extracts were dried and concentrated to give the title compound. MS (m/z): 505 (M+H)+.

Workup

  1. customat 0° C
  2. temperatureThe mixture was warmed up
  3. temperatureThe reaction mixture was then cooled to 0° C.
  4. additionAfter the completion of the addition
  5. stirringthe reaction mixture was stirred
  6. temperatureat reflux for 4 hours
  7. temperaturecooled to ambient temperature
  8. customquenched with H2O
  9. extractionextracted with EtOAc
  10. customThe combined extracts were dried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-a0402de93ee045229d4ca448898cbbd3
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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