(5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol → 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde

HRID 859616Notes

Reaction equation

HRID 859616 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([CH2:12][OH:13])[N:11]=[C:4]2[N:3]=1>ClCCCl.C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([CH:12]=[O:13])[N:11]=[C:4]2[N:3]=1

Participants

4

Reactant 1

HCID 44141733(5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol

Product 1

HCID 236352265,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeYield 77%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A slurry of 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-methanol (0.3 g, 1.7 mmol) from step 7 above and IBX (1.4 g, 5.0 mmol) in 1,2-dichloroethane (22 mL) was stirred at 80° C. for 18 hours. The reaction was cooled to room temperature, and diluted with 100 mL CH2Cl2. After the solids were removed by filtration, the solvent was removed by rotary evaporation to give a yellow solid. The solid was purified by flash chromatography to give the desired product (229 mg, 77% yield). 1H NMR (CDCl3) δ: 2.72 (s, 3 H), 2.86 (s, 3 H), 6.96 (s, 1 H), 10.24 (s, 1 H).

Workup

  1. customAfter the solids were removed by filtration
  2. customthe solvent was removed by rotary evaporation
  3. customto give a yellow solid
  4. customThe solid was purified by flash chromatography

Sources & evidence

ORD record
ord-37ccb550fc8a4434ad306f498050b60f
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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