Acetic Anhydride → HCID 68916487, compound

HRID 883517Notes

Reaction equation

HRID 883517 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[N:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[N:12][N:13]=2)=[N:6][CH:7]=1.CCN(CC)CC.[CH3:27][C:28](OC(C)=O)=[O:29]>>[C:28]([N:10]1[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[N:12][N:13]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][N:6]=2)[NH:9]1)(=[O:29])[CH3:27]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 575524811055983-02-2

Product 1

HCID 68916487HCID 68916487, compoundYield 56%

Conditions

Temperature
0 °C

Procedure

A dry round-bottom flask was charged with 3-(5-aminopyridin-2-yl)-6-(pyridin-2-yl)-1,2,4,5-tetrazine (0.020 g, 0.08 mmol) and cooled to 0° C. Et3N (0.012 mL, 0.12 mmol) was added followed by Ac2O (0.6 mL), which was added dropwise via syringe. The reaction mixture was allowed to stir at room temperature for 3 h and then concentrated under reduced pressure. The crude residue was chromatographed on silica gel using a gradient (0-100%) of acetone in hexanes as the eluent to give 13 mg (0.04 mmol, 56%) of the title compound as a reddish pink solid.

Workup

  1. additionwas added dropwise via syringe
  2. concentrationconcentrated under reduced pressure
  3. customThe crude residue was chromatographed on silica gel using a gradient (0-100%) of acetone in hexanes as the eluent

Sources & evidence

ORD record
ord-87255b90c0784716a5b83faf36afb9d2
Source dataset
uspto-grants-2012_08
Patent number
US08236949B2

Reaction notes

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