2-Bromopropanedial → 6-Bromo-2-tert-butyl-[1,2,4]triazolo[1,5-a]pyrimidine

HRID 2042190Notes

Reaction equation

HRID 2042190 reaction equation
[C:1]([C:5]1[N:9]=[C:8]([NH2:10])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:11][CH:12]([CH:15]=O)[CH:13]=O>C(O)(=O)C>[Br:11][C:12]1[CH:13]=[N:10][C:8]2[N:7]([N:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:9]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 749452-BromopropanedialHCID 178441978HCID 178441978, compound

Product 1

HCID 583167046-Bromo-2-tert-butyl-[1,2,4]triazolo[1,5-a]pyrimidineYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

3-tert-Butyl-1H-1,2,4-triazol-5-amine (CAS 202403-45-0) (35%, 13 g, 32.5 mmol) was dissolved in acetic acid (50 ml) and 2-bromomalonaldehyde (7.35 g, 48.7 mmol, 1.5 equiv.) was added. The reaction mixture was stirred for 3 hours at 60° C. The reaction mixture was evaporated and neutralized with saturated NaHCO3 solution 2N and extracted two times with dichloromethane. The organic extracts were dried with sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography on 70 g silica gel (heptane:EtOAc 100:0->50:50). The desired 6-bromo-2-tert-butyl-[1,2,4]triazolo[1,5-a]pyrimidine (6.83 g, 83% yield) was obtained as a white solid, MS: m/e=255.0/257.1 (M+H+).

Workup

  1. customThe reaction mixture was evaporated
  2. extractionextracted two times with dichloromethane
  3. dry with materialThe organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by flash chromatography on 70 g silica gel (heptane:EtOAc 100:0->50:50)

Sources & evidence

ORD record
ord-fa526b174780448899ab0de91aaf5e3f
Source dataset
uspto-grants-2013_11
Patent number
US08586581B2

Reaction notes

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