tert-Butyl mercaptan → HCID 16753771, compound

HRID 1992441Notes

Reaction equation

HRID 1992441 reaction equation
[CH3:1][C:2]([SH:5])([CH3:4])[CH3:3].[H-].[Na+].[Br:8][C:9]1[N:10]=[C:11](Br)[N:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[C:13]=12>CN(C=O)C>[Br:8][C:9]1[N:10]=[C:11]([S:5][C:2]([CH3:4])([CH3:3])[CH3:1])[N:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[C:13]=12

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 24758Sodium hydrideHCID 16753769HCID 16753769, compound

Product 1

HCID 16753771HCID 16753771, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A bohdan block vessel was charged with 2-methyl-2-propanethiol (20 uL, 0.0002 mol) in DMF (2 mL) and the reaction mixture was degassed 3×. Sodium hydride (0.01 g, 0.0004 mol) was then added and the reaction mixture was stirred at rt for 10 min. 1,3-Dibromo-imidazo[1,5-a]pyrazin-8-ylamine (30 mg, 0.0001 mol) was added to the reaction mixture and the reaction mixture was heated at 70° C. overnight. The reaction mixture turned red in color as the reaction progressed. The reaction mixture was concentrated and purified by prep TLC using a mixture of 7 N5% NH3 in MeOH/DCM to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD-d4): δ=1.37 (s, 9H), 7.13 (d, J=5.05 Hz, 1H), 7.84 (d, J=5.05 Hz, 1H). MS(ES+): m/z 303.02 (100)[MH+]. HPLC: tR=2.30 min (Open Lynx polar—5 min).

Workup

  1. customthe reaction mixture was degassed 3×
  2. temperaturethe reaction mixture was heated at 70° C. overnight
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by prep TLC
  5. additiona mixture of 7 N5% NH3 in MeOH/DCM

Sources & evidence

ORD record
ord-c1428dcda5da43c4a5326009fc53d468
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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