(2S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazine → Pyrazine, 2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)-5-[(2,4,5-trifluorophenyl)methyl]-, (2S,5R)-

HRID 1272367Notes

Reaction equation

HRID 1272367 reaction equation
[CH3:1][O:2][C:3]1[C@H:4]([CH:11]([CH3:13])[CH3:12])[N:5]=[C:6]([O:9][CH3:10])[CH2:7][N:8]=1.[F:14][C:15]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:16]=1[CH2:17]Br>>[CH3:1][O:2][C:3]1[C@H:4]([CH:11]([CH3:13])[CH3:12])[N:5]=[C:6]([O:9][CH3:10])[C@@H:7]([CH2:17][C:16]2[CH:19]=[C:20]([F:24])[C:21]([F:23])=[CH:22][C:15]=2[F:14])[N:8]=1

Participants

3

Reactant 2

HCID 736065(2S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazineHCID 27770572,4,5-Trifluorobenzyl Bromide

Product 1

HCID 11290377Pyrazine, 2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)-5-[(2,4,5-trifluorophenyl)methyl]-, (2S,5R)-Yield 62.7%

Procedure

The title compound (3.81 g) was prepared from 3.42 g (18.5 mmol) of (2S)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine and 5 g (22.3 mmol) of 2,4,5-trifluorobenzyl bromide using the procedure described for Intermediate 2, Step A. 1H NMR (500 MHz, CDCl3) δ 7.01 (m, 1H), 6.85 (m, 1H), 4.22 (m, 1H), 3.78 (m, 3H), 3.64 (m, 3H), 3.61 (m, 1H), 3.20 (m, 1H), 2.98 (m, 1H), 2.20 (m, 1H), 0.99 (d, 3H, J=8 Hz), 0.62 (d, 3H, J=8 Hz).

Sources & evidence

ORD record
ord-6f2299aeda88409994e5fcc5456a9b54
Source dataset
uspto-grants-2007_04
Patent number
US07208498B2

Reaction notes

Loading…