1-Phenethylamine, (-)- → HCID 76723649, compound

HRID 1821643Notes

Reaction equation

Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[C:10]1([C@@H:16]([NH2:18])[CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCOCC1>[Br:8][C:6]1[N:7]=[C:2]([NH:18][CH:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:17])[C:3]([NH2:9])=[N:4][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3,5-dibromopyrazin-2-ylamine (1.0 g; 3.95 mmol) in anhydrous dioxane (10 mL) was added (S)-(−)-1-phenylethylamine (0.51 mL; 3.95 mmol) at room temperature. The solution was heated to 100° C. and stirred for 20 h. After concentration under reduced pressure, the resultant residue was purified by flash chromatography [silica gel, hexanes/ethyl acetate (2:1)] to afford 5-bromo-N3-(1-phenylethyl)pyrazine-2,3-diamine as a brown solid (0.69 g; 60%). 1H NMR (300 MHz, DMSO): δ 7.37-7.29 (m, 5H), 7.14 (s, 1H), 6.84 (d, J=7.2 Hz, 1H), 6.29 (s, 2H), 5.10-5.05 (m, 1H), 1.47 (d, J=6.9 Hz, 3H).

Workup

concentrationAfter concentration under reduced pressure
customthe resultant residue was purified by flash chromatography [silica gel, hexanes/ethyl acetate (2:1)]

Sources & evidence

ORD record: ord-b78e5f8a38a24ccbbbf327b61e609051
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608622B2

Reaction notes

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