Nitrogen → 5-Methoxy-1,2,4-triazine-6-methanamine

HRID 449017Notes

Reaction equation

HRID 449017 reaction equation
N#N.[N:3]([CH2:6][C:7]1[N:12]=[N:11][CH:10]=[N:9][C:8]=1[O:13][CH3:14])=[N+]=[N-]>[Pd].CO>[CH3:14][O:13][C:8]1[N:9]=[CH:10][N:11]=[N:12][C:7]=1[CH2:6][NH2:3]

Participants

5

Reactant 2

HCID 947NitrogenHCID 866360246-(Azidomethyl)-5-methoxy-1,2,4-triazine

Product 1

HCID 552905845-Methoxy-1,2,4-triazine-6-methanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A flask filled with N2 was charged with 6-(azidomethyl)-5-methoxy-1,2,4-triazine (15.0 g, 0.0903 mol) and Pd/C (10%) (3.20 g) followed by MeOH (480 mL). The suspension was purged with N2. The reaction was then stirred under H2 (1 atm) at rt for 5 h. The inorganics were filtered off, the solvent was removed under reduced pressure to give 1-(5-methoxy-[1,2,4]triazin-6-yl)-methylamine which was used for next step without any further purification.

Workup

  1. customThe suspension was purged with N2
  2. filtrationThe inorganics were filtered off
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b829347c844845b08b2d6e3fe7dac954
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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