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

HRID 859736Notes

Reaction equation

HRID 859736 reaction equation
[Cl: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>[Cl: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 23056782(6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol

Product 1

HCID 587625546-Chloro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (6-chloro[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol (9.86 g, 53.4 mmol), TEMPO (626 mg, 7.2 mmol), iodobenzene diacetate (18.9 g, 59 mmol) in CH2Cl2 (75 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 as a white solid (8.72 g, 90%). 1H NMR (300 MHz, CDCl3) δ: 8.93 (d, J=2.45 Hz, 1 H), 8.99 (d, J=2.64 Hz, 1 H), 10.25 (s, 1 H). MS (APCI): 183.0, 195.0 (M+H+).

Workup

  1. customto precipitate the product as a white solid (8.72 g, 90%)

Sources & evidence

ORD record
ord-0d6663eda92e40f19da81caf4339d0c5
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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