tert-Butyl methyl ether → 6-Bromo-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde

HRID 1453136Notes

Reaction equation

HRID 1453136 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH2:11][OH:12])[N:10]=2)[CH:7]=1.C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C.CC1(C)N([O])C(C)(C)CCC1.CC(OC)(C)C>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH:11]=[O:12])[N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 76724Iodobenzene diacetateHCID 2724126TempoHCID 57527274{6-Bromo-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}methanol

Product 1

HCID 575272776-Bromo-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of (6-bromo-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-methanol (6.5 g, 28.51 mmol) from step 1 above in dichloromethane (60 mL) was added PhI(OAc)2 (10.1 mg, 31.4 mmol) and with catalytic TEMPO (334 mg, 2.14 mmol). After reaction at room temperature for 3 hours, the reaction is complete. MTBE is added slowly (50 mL) to crystallize the product, filtration followed by drying the product by vacuum oven overnight. The filtrate was concentrated and purified by flash chromatography (2% MeOH in CH2Cl2) to give the desired product as light white solid (combine total 4.8 g, 75% yield). 1H NMR (300 MHz, CDCl3) □ ppm 8.96 (d, J=2.45 Hz, 1H) 9.09 (d, J=2.45 Hz, 1H) 10.22 (s, 1H). MS: (APCI) 228 (M+H)

Workup

  1. customAfter reaction at room temperature for 3 hours
  2. customto crystallize
  3. filtrationthe product, filtration
  4. customby drying the product by vacuum oven overnight
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash chromatography (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-3475274e0d514b748f50e3cc8632e45a
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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