N-methyl-2-pyrrolidone → HCID 178503307, compound

HRID 1019714Notes

Reaction equation

HRID 1019714 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:13])[C:9]([OH:11])=[N:10][C:5]2=[N:4][CH:3]=1.[CH3:20][S-:21].[Na+].CN1CCCC1=O>CCOC(C)=O>[CH3:20][S:21][C:2]1[N:7]=[C:6]2[N:8]([C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:13])[C:9]([OH:11])=[N:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 4378561Sodium methanethiolateHCID 178461678HCID 178461678, compound

Product 1

HCID 178503307HCID 178503307, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A thick-walled microwave bottle equipped with a stirbar was charged with (S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol (1.0 equiv), sodium thiomethoxide (4.5 equiv), and N-methylpyrrolidone (10 volume equivalents). The bottle was fitted with a septum and cap and heated to 180° C. in a microwave for 30 min. The reaction mixture was then diluted with 100 volume equivalents of EtOAc and washed with 4×100 volume equivalents of water and 1×100 volume equivalents of brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Reverse-phase preparative HPLC (20%-80% MeCN/H2O) provided the title compound (24%) as a white solid. LCMS m/z (APCI)=287.1 (M+H).

Workup

  1. customA thick-walled microwave bottle equipped with a stirbar
  2. customThe bottle was fitted with a septum
  3. customcap
  4. washwashed with 4×100 volume equivalents of water and 1×100 volume equivalents of brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c53701aa7fce4e5b96f819ac0cb175d6
Source dataset
uspto-grants-2014_05
Patent number
US08716291B2

Reaction notes

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