Formaldehyde → 5-Bromo-2-methyl-8-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrazine

HRID 1045749Notes

Reaction equation

HRID 1045749 reaction equation
[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[N:10]=[C:6]2[C:5]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[N:4][CH:3]=1.[CH2:18](Cl)Cl.C=O.C([O-])(O)=O.[Na+]>CO>[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[N:10]=[C:6]2[C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 584470575-Bromo-2-methyl-8-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrazine

Product 1

HCID 584469845-Bromo-2-methyl-8-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrazineYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 100 mL round bottom flask was charged with 5-bromo-2-methyl-8-(piperazin-1-yl)-[1,2,4]-triazolo[1,5-a]pyrazine (0.5 g, 1.7 mmol), CH2Cl2 (20 mL), MeOH (10 mL), 40% aqueous formaldehyde (2 mL) and NaBH3(CN) (0.5 g, 8.0 mmol). The resulting solution was stirred at room temperature for 0.5 h. Work-up: the reaction mixture was poured into saturated aqueous NaHCO3 and extracted with CH2Cl2 (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with 1-10% MeOH in CH2Cl2, to afford 0.4 g (76%) of the product as a yellow solid. MS m/z: 311 (M+H+).

Workup

  1. extractionextracted with CH2Cl2 (50 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel with 1-10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-7e7f697cf5fe49378143303cecd53064
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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