Ethanol → 8-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-amine

HRID 570608Notes

Reaction equation

HRID 570608 reaction equation
Cl.NO.C(O)C.CC[N:9](C(C)C)C(C)C.[Cl:16][C:17]1[C:18]([NH:23][C:24]([NH:26]CCOC(=O)C)=O)=[N:19][CH:20]=[CH:21][N:22]=1>CO>[Cl:16][C:17]1[C:18]2[N:19]([N:9]=[C:24]([NH2:26])[N:23]=2)[CH:20]=[CH:21][N:22]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 866943461-(3-Chloro-pyrazin-2-yl)-3-acetoxyethyl-urea

Product 1

HCID 772310108-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.6 g (23.2 mmol) hydroxylamine hydrochloride are suspended in 20 ml of a 1:1 mixture of ethanol and methanol. Then 2.4 ml (13.9 mmol) DIPEA are added and the mixture is stirred at ambient temperature for 1 h. At that time, the reaction suspension is added to 2 g (4.6 mmol, 62% content) 1-(3-chloro-pyrazin-2-yl)-3-acetoxyethyl-urea and refluxed for 2 h. The reaction is cooled to room temperature filtered and washed with water. The product is isolated after drying in a vacuum oven (60° C.) (790 mg, 4.65 mmol, 100%); LCMS (method C): mass found (M+H+, 170), HPLC (method D) Rt (min): 2.14 area % 100 (220 nm); 1H NMR (400 MHz, DMSO-d6) δ [ppm] 8.83 (d, J=4.3, 1H), 7.92 (d, J=4.3, 1H), 6.77 (s, 2H).

Workup

  1. temperaturerefluxed for 2 h
  2. temperatureThe reaction is cooled to room temperature
  3. filtrationfiltered
  4. washwashed with water
  5. customThe product is isolated
  6. customafter drying in a vacuum oven (60° C.) (790 mg, 4.65 mmol, 100%)

Sources & evidence

ORD record
ord-748871b7e4054d3983be5622b515726f
Source dataset
uspto-grants-2015_05
Patent number
US09023851B2

Reaction notes

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