Hydrochloric Acid → (S)-1-(4-(pyrimidin-5-yloxy)phenyl)ethanamine

HRID 1850176Notes

Reaction equation

HRID 1850176 reaction equation
CC(S([NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:18]=[N:19][CH:20]=[N:21][CH:22]=2)=[CH:12][CH:11]=1)[CH3:9])=O)(C)C.Cl.O1CCOCC1>>[N:19]1[CH:18]=[C:17]([O:16][C:13]2[CH:12]=[CH:11][C:10]([C@@H:8]([NH2:7])[CH3:9])=[CH:15][CH:14]=2)[CH:22]=[N:21][CH:20]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 867302022-methyl-N-((S)-1-(4-(pyrimidin-5-yloxy)phenyl)ethyl)propane-2-sulfinamide

Product 1

HCID 86730203(S)-1-(4-(pyrimidin-5-yloxy)phenyl)ethanamineYield 118.8%

Procedure

To 2-methyl-N—((S)-1-(4-(pyrimidin-5-yloxy)phenyl)ethyl)propane-2-sulfinamide (55 mg, 0.172 mmol) was added 4M HCl in dioxane (800 μL, 3.20 mmol) to give a white suspension. This resulting mixture was stirred at room temperature for ˜35 min and concentrated under reduced pressure to provide crude (S)-1-(4-(pyrimidin-5-yloxy)phenyl)ethanamine (44 mg) as its HCl salt, which was used without further purification. LCMS m/z 217.1 (M+H)+, Rt 0.37 min.

Workup

  1. customto give a white suspension
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-afd09d2c690c4fa88893643f894c8eb1
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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