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

HRID 1453075

Reaction equation

HRID 1453075 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.CC1(C)N([O])C(C)(C)CCC1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.COC(C)(C)C>C(Cl)Cl>[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 4

HCID 15413tert-Butyl methyl etherHCID 2724126TempoHCID 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-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (6-methyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol (15.7 g, 95.6 mmol), TEMPO (1.12 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 additional amount of the aldehyde product as a while solid (12 g, 80%). 1H NMR (300 MHz, CDCl3) δ: 2.54 (m, 3H), 8.73 (m, 1H), 8.85 (m, 1H), 10.23 (m, 1H). MS (APCI, M+H+): 163.1.

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-f19d874ba2eb4f9fb227e20fc4ca5d55
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Linked notes

Loading…