Triethylamine → HCID 67120781, compound

HRID 552380Notes

Reaction equation

HRID 552380 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.C([N:11](CC)CC)C.[C:16](Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[C:16]([C:6]1[CH:7]=[CH:2][N:3]=[C:4]([NH2:8])[C:5]=1[NH2:11])(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 88612,6-DiaminopyridineHCID 62493Pivaloyl chloride

Product 1

HCID 67120781HCID 67120781, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,6-diaminopyridine (10 g, 91.743 mmol) and triethylamine (11.14 g, 110.091 mmol, 1.2 equiv.) in DCM (100 mL) at 0° C. is added dropwise a solution of pivaloyl chloride (12.11 g, 100.917 mmol, 1.1 equiv.) in DCM (50 mL) over 2 hours. After completion of the addition the mixture is allowed to warm to room temperature over 30 minutes, at which point LC-MS shows full conversion to the desired material. The mixture is filtered to remove the triethylammonium chloride, and the solvent is removed under vacuum to afford a solid that is not processed further.

Workup

  1. additionAfter completion of the addition the mixture
  2. filtrationThe mixture is filtered
  3. customto remove the triethylammonium chloride
  4. customthe solvent is removed under vacuum
  5. customto afford a solid

Sources & evidence

ORD record
ord-7faab40a7999444f90d1218edd1f4103
Source dataset
uspto-grants-2011_05
Patent number
US07951818B2

Reaction notes

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