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

HRID 1438201Notes

Reaction equation

HRID 1438201 reaction equation
[CH3:1][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(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.C(OC)(C)(C)C>C(Cl)Cl.CC1(C)N([O])C(C)(C)CCC1>[CH3:1][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 3

HCID 15413tert-Butyl methyl etherHCID 12217721Iodo benzene diacetateHCID 58762279(6-Methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol

Product 1

HCID 587626196-Methyl-[1,2,4]triazolo[1,5-A]pyrimidine-2-carbaldehydeYield 80%

Reagents, catalysts & solvents 2

HCID 2724126TempoCatalystHCID 6344DichloromethaneSolvent

Procedure

A slurry of (6-methyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol (15.7 g, 95.6 mmol) from step 1 above, TEMPO (112 mg, 7.2 mmol), iodobenzene diacetate (33.9 g, 105.2 mmol) in CH2Cl2 (100 mL) was stirred at room temperature for 2 hours. Once the reaction was deemed complete, methyl tert-butyl ether (50 mL) was added slowly to precipitate the product. The concentrated mother liquor was introduced into a silica gel column and eluted with 2% MeOH/CH2Cl2 to give an additional amount of the aldehyde product as a white solid (12 g, 80%). 1H NMR (CDCl3) □: 2.54 (s, 3H), 8.73 (s, 1H), 8.85 (s, 1H), 10.23 (s, 1H).

Workup

  1. customto precipitate the product
  2. additionThe concentrated mother liquor was introduced into a silica gel column
  3. washeluted with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-f031bfb8c86d418cbf28a51bd0c16da9
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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