Ammonia → HCID 16753769, compound

HRID 1992438Notes

Reaction equation

HRID 1992438 reaction equation
[NH3:1].[Br:2][C:3]1[N:4]=[C:5]([Br:13])[N:6]2[CH:11]=[CH:10][N:9]=[C:8](Cl)[C:7]=12.CC(O)CC>O>[Br:2][C:3]1[N:4]=[C:5]([Br:13])[N:6]2[CH:11]=[CH:10][N:9]=[C:8]([NH2:1])[C:7]=12

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6568(+-)-2-ButanolHCID 58902039HCID 58902039, compound

Product 1

HCID 16753769HCID 16753769, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 M of NH3 in H2O(10 mL) was added to a suspension of 1,3-Dibromo-8-chloro-imidazo[1,5-a]pyrazine (1.726 g, 0.007425 mol) in 2-Butanol (7.49 mL, 0.0817 mol). The mixture was heated in an oil bath set at 90° C. overnight. The reaction mixture was concentrated in vacuo and purified by flash column chromatography using 1→6% MeOH in DCM to obtain the title compound as a yellow solid. MS (ES+): m/z 294.83 (85) [MH+]. HPLC: tR=1.58 min (Open Lynx polar—5 min). 1H NMR (400 MHz, CD3OD):δ=7.10 (d, J=5.05 Hz, 1H), 7.43 (d, J=5.05 Hz, 1H)

Workup

  1. temperatureThe mixture was heated in an oil bath
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-438d2e0f851a42cbb95eabd86e4daa1e
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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