Methanol → HCID 63609987, compound

HRID 524868Notes

Reaction equation

HRID 524868 reaction equation
[CH3:1][C:2]1([CH3:15])[NH:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH2:14])[CH2:3]1.[H-].[Na+].[CH3:18]I.CO>CN(C=O)C>[CH3:1][C:2]1([CH3:15])[N:7]([CH3:18])[CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH2:14])[CH2:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86720927HCID 86720927, compound

Product 1

HCID 63609987HCID 63609987, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 4-(3,3-dimethylpiperazin-1-yl)pyridin-3-amine (prepared according to methods similar to the one depicted in Preparation N-1) (120 mg, 0.5817 mmol) in DMF (2 mL) at 0° C. was added NaH (20.94 mg, 0.5235 mmol). The reaction mixture was stirred for 10 mins at 0° C. then MeI (276.3 uL, 0.5526 mmol, 2M in TBDME) was added. The reaction mixture was allowed to warm to RT and was stirred for 2 hours at RT. The crude was loaded onto a MeOH pre-washed SCX column, rinsed with MeOH and the product was released with methanolic ammonia. The ammonia extracts were concentrated under reduced pressure to yield 4-(3,3,4-trimethylpiperazin-1-yl)pyridin-3-amine (128 mg, 73%). MS (ES+) 221.1.

Workup

  1. temperatureto warm to RT
  2. stirringwas stirred for 2 hours at RT
  3. washrinsed with MeOH
  4. concentrationThe ammonia extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-ac62dab0808c461db42095e5a6136882
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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