Cyclopentanethiol → 2-Amino-5-phenyl-3-cyclopentylthiopyrazine

HRID 1034595Notes

Reaction equation

HRID 1034595 reaction equation
[CH:1]1([SH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[NH2:9][C:10]1[C:15](Br)=[N:14][C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][N:11]=1>C(#N)C>[NH2:9][C:10]1[C:15]([S:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:14][C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 15510CyclopentanethiolHCID 24758Sodium hydrideHCID 124535523-Bromo-5-phenylpyrazin-2-amine

Product 1

HCID 680079742-Amino-5-phenyl-3-cyclopentylthiopyrazineYield 67.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of cyclopentanethiol (0.18 g, 1.80 mmol) in dry acetonitrile (20 mL), sodium hydride (NaH) (0.04 g, 1.80 mmol) was added the resulting mixture was stirred for 15 min. After this time 2-amino-3-bromo-5-phenylpyrazine 17b (0.15 g, 0.6 mmol) was added and the mixture heated at 80° C. for 2 h, cooled and quenched with water. Then EtOAc was added and the organic layer was anidrified over Na2SO4, filtered and the solvent removed under reduced pressure to get a crude that was purified by flash chromatography using dichloromethane-EtOAc (9:1 v/v) as eluent, to obtain 0.11 g of the title compound 18n as a yellow solid (mp 92-94° C., 67% yield). 1H-NMR (CDCl3): 1.68-1.83 (m, 6H), 2.28-2.31 (m, 2H), 4.21-4.28 (m, 1H), 4.93 (br s, 2H), 7.32-7.35 (m, 1H), 7.41-7.45 (m, 2H), 7.91-7.93 (m, 2H), 8.20 (s, 1H). MS (ESI): m/z 272 (Mile).

Workup

  1. temperaturecooled
  2. customquenched with water
  3. additionThen EtOAc was added
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customto get a crude that
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-e2fd2462842b4a568c7b55a8036e5515
Source dataset
uspto-grants-2013_10
Patent number
US08546147B2

Reaction notes

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