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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 524868Generated: October 30, 2026

Methanol → HCID 63609987, compound

https://huagongshe.com/reaction/524868

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
ReactantHCID 86720927HCID 86720927—
SolventDimethylformamideHCID 6228—
ProductHCID 63609987HCID 6360998773%

Reaction Conditions

Temperature0 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09340546B2
Source datasetuspto-grants-2016_05
ORD IDord-ac62dab0808c461db42095e5a6136882
Source noteuspto-grants-2016_05