Ethanol → Hexane ethanol diethylamine

HRID 657759Notes

Reaction equation

HRID 657759 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([NH2:10])[CH3:9])=[CH:4][N:3]=1.[CH3:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:17][CH2:18][OH:19]>>[CH3:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:17][CH2:18][OH:19].[NH:3]([CH2:4][CH3:5])[CH2:2][CH3:1].[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][N:3]=1.[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 8058HexaneHCID 552838311-(2-Methylpyrimidin-5-yl)ethanamine

Product 3

HCID 21881120Hexane ethanol diethylamineHCID 55281681(R)-1-(2-Methyl-5-pyrimidinyl)ethanamineHCID 58103572(S)-1-(2-methylpyrimidin-5-yl)ethanamine

Procedure

Racemic 1-(2-methylpyrimidin-5-yl)ethanamine (2.78 g, 20.3 mmol) was resolved by chiral HPLC (sample preparation: sample was dissolved in 4 mL EtOH (heated) and 8 mL hexane was added). HPLC conditions: CHIRALPAK AD-H column at 0° C. [ice-bath], 20×250 mm, hexane/EtOH/Et2NH [85:15:0.03] at 20 mL/min, UV detection at 230 nm) to yield (S)-1-(2-methylpyrimidin-5-yl)ethanamine (1.19 g, >99% ee) and (R)-1-(2-methylpyrimidin-5-yl)ethanamine (1.16 g, >99% ee).

Sources & evidence

ORD record
ord-203767d19294425a8c94562c6b0cbe45
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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