Dimethylformamide → HCID 16753682, compound

HRID 1992437Notes

Reaction equation

HRID 1992437 reaction equation
[CH2:1]([SH:4])[CH2:2]C.[CH3:5]N(C=O)C.[Br:10][C:11]1[N:12]=[C:13](Br)[N:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[C:15]=12>>[Br:10][C:11]1[N:12]=[C:13]([S:4][CH:1]([CH3:2])[CH3:5])[N:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[C:15]=12

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7848Propyl mercaptanHCID 16753769HCID 16753769, compound

Product 1

HCID 16753682HCID 16753682, compound

Procedure

A bohdan block vessel was charged with propanethiol (0.010 g, 0.00014 mol) in DMF (1 mL, 0.01 mol) and the reaction mixture was degassed 3×. Sodium hydride was then added and the reaction mixture was stirred at rt for 10 min. 1,3-Dibromo-imidazo[1,5-a]pyrazin-8-ylamine (20 mg, 0.00007 mol) was added and the reaction mixture was heated at 70° C. for 4 h. The reaction mixture was concentrated in vacuo to give the title compound as a brown solid. 1H NMR (400 MHz, CD3OD-d4): δ=1.09 (d, J=6.82 Hz, 9H), 1.28 (d, 9H), 3.45-3.57 (m, 1H), 7.10 (d, J=5.05 Hz, 1H), 7.69 (d, J=5.05 Hz, 1H). MS(ES+): m/z 288.95 (100)[MH+]. HPLC: tR=2.13 min (Open Lynx polar—5 min).

Workup

  1. customthe reaction mixture was degassed 3×
  2. additionSodium hydride was then added
  3. temperaturethe reaction mixture was heated at 70° C. for 4 h
  4. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-34c8fc27934e48aba59a040d0752fe57
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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