Ethyl orthoformate → Tert-butyl 4-(5-bromo-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate

HRID 1045709Notes

Reaction equation

HRID 1045709 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([NH:21][NH2:22])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH:23](OCC)(OCC)OCC>>[Br:1][C:2]1[N:3]2[CH:23]=[N:22][N:21]=[C:4]2[C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 58447020Tert-butyl 4-(5-bromo-3-hydrazinylpyrazin-2-yl)piperazine-1-carboxylate

Product 1

HCID 58447004Tert-butyl 4-(5-bromo-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylateYield 69%

Conditions

Temperature
130 °C

Procedure

A 50 mL round bottom flask was charged with tert-butyl 4-(5-bromo-3-hydrazinylpyrazin-2-yl)piperazine-1-carboxylate (5.8 g, 20 mmol) and triethyl orthoformate (60 mL). The resulting solution was heated at 130° C. for 3 h. TLC indicated a complete conversion. The solvent was evaporated and the residue was purified by flash column chromatography on silica gel with 2% methanol in dichloromethane, to afford 5.3 g (69%) of the product as a yellow solid. MS m/z: 383 (M+H+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash column chromatography on silica gel with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-c1aace705bb44a5c8bf16752747c1b5c
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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