Diisopropylethylamine → 6-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 250019Notes

Reaction equation

HRID 250019 reaction equation
C(OC([NH:6][C:7]([NH2:9])=S)=O)C.[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=1.Cl.NO.CCN(C(C)C)C(C)C>C(O)C.CO>[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([N:6]=[C:7]([NH2:9])[N:18]=2)[CH:17]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 866352895-Methoxypyridin-2-amine ethoxycarbonyl thiourea

Product 1

HCID 468640666-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amineYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To 5-methoxypyridin-2-amine ethoxycarbonyl thiourea (10.21 g, 40 mmol) in ethanol (57 mL) and methanol (57 mL) was added hydroxylamine hydrochloride (14 g, 200 mmol) and Hunig's Base (21 mL, 120 mmol). The mixture was stirred at room temperature for 2 hours, and then heated at 60° C. for 4 hours. The reaction was cooled to room temperature and filtered to remove solids. It was concentrated in vacuo and then suspended in chloroform. The solids were filtered off to yield 6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amine (6.05 g, 33.2 mmol, 83% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.30 (1 H, d, J=1.83 Hz), 7.24-7.32 (1 H, m), 7.16-7.23 (1 H, m), 5.82 (2 H, br. s.), 3.78 (3 H, s). MS (LC/MS) R.T.=0.53; [M+H]+=165.2.

Workup

  1. temperatureheated at 60° C. for 4 hours
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered
  4. customto remove solids
  5. concentrationIt was concentrated in vacuo
  6. filtrationThe solids were filtered off

Sources & evidence

ORD record
ord-b2aabe3a5d4b4cb38bddd3bf5a57930e
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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