Hydrochloric Acid → (S)-1-pyrimidin-2-yl propylamine hydrochloride

HRID 926373Notes

Reaction equation

HRID 926373 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C@@H:7]([NH:10][S@](C(C)(C)C)=O)[CH2:8][CH3:9].[ClH:17].O>CO.O1CCOCC1>[ClH:17].[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C@@H:7]([NH2:10])[CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 89734173(S)-2-methyl-propane-2-sulfinic acid ((S)-1-pyrimidin-2-yl-propyl)amide

Product 1

HCID 89726467(S)-1-pyrimidin-2-yl propylamine hydrochlorideYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (S)-2-methyl-propane-2-sulfinic acid ((S)-1-pyrimidin-2-yl-propyl)-amide (Comp. No. 14a) (1.4 g, 5.8 mmol) in methanol was added 4 M hydrogen chloride in dioxane (4.35 ml) and the mixture was stirred for 1 h at 25° C. Water (100 ml) was added and the aqueous phase was washed with methyl tert-butyl ether. The aqueous layer was freeze-dried to give 0.919 g (75%) of (S)-1-pyrimidin-2-yl-propylamine hydrochloride. LC/MS (method 5): Rt=0.69 min; m/z=138.15 (M+H+).

Workup

  1. washthe aqueous phase was washed with methyl tert-butyl ether
  2. customThe aqueous layer was freeze-dried

Sources & evidence

ORD record
ord-6202e73cde504c6d8bed0cdbbe8b63b1
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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