Ammonia → HCID 11219056, compound

HRID 1244641Notes

Reaction equation

HRID 1244641 reaction equation
[NH3:1].Cl[C:3]1[C:8]([CH3:9])=[N:7][N:6]2[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[N:11][N:12]=[C:5]2[N:4]=1>CO>[NH2:1][C:3]1[C:8]([CH3:9])=[N:7][N:6]2[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[N:11][N:12]=[C:5]2[N:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21919323HCID 21919323, compound

Product 1

HCID 11219056HCID 11219056, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

NH3 gas was bubbled through a solution of 4-(7-chloro-6-methyl-[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-ylmethyl)-phenol (70 mg, 0.25 mmol) in methanol (5 mL) at 0° C. The saturated solution was stirred at 70° C. until the starting material disappeared. After evaporation of solvent, the residue was purified on a silica gel column eluting with 10% methanol in dichloromethane to provide 4-(7-amino-6-methyl-[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-ylmethyl)-phenol (35 mg). 1H-NMR (400 MHz, DMSO-d6) δ 9.22 (s, 1H), 7.05 (d, 2H), 6.65 (d, 2H), 4.12 (s, 2H), 2.35 (s, 3H). MS (m/z) 257 [M+1].

Workup

  1. customAfter evaporation of solvent
  2. customthe residue was purified on a silica gel column
  3. washeluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-9ee41a706a804c24979583d648e88649
Source dataset
uspto-grants-2006_10
Patent number
US07122548B2

Reaction notes

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