1H-1,2,4-Triazole → HCID 178474427, compound

HRID 1774112Notes

Reaction equation

HRID 1774112 reaction equation
[C:1]([NH:4][C:5]1[N:14]=[C:13](O)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:16])[CH:11]=2)[N:6]=1)(=[O:3])[CH3:2].[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1.C(N(C(C)C)CC)(C)C.O=P(Cl)(Cl)Cl>C(#N)C>[C:1]([NH:4][C:5]1[N:14]=[C:13]([C:21]2[N:20]=[CH:19][NH:18][N:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:16])[CH:11]=2)[N:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178474466HCID 178474466, compound

Product 1

HCID 178474427HCID 178474427, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2-acetamido-6-bromo-4-hydroxy-quinazoline (2.82 g, 10 mmol) and 1,2,4-triazole (6.9 g, 100 mmol) in acetonitrile (100 ml) was added diisopropylethylamine (3.5 ml, 30 mmol) and POCl3 (2.8 ml, 30 mmol). The mixture was stirred at room temperature for 12 hours. The precipitate was collected, washed with ethanol, diethylether, and dried over P2O5 in a vacuum dessicator to yield the title compound as yellow solid (3.3 g). The crude product was used in the following reaction without further purification and was characterized by its mass spectrum as follows: MS (m/z): 333 ([M+H]+, 100).

Workup

  1. customThe precipitate was collected
  2. washwashed with ethanol, diethylether
  3. dry with materialdried over P2O5 in a vacuum dessicator

Sources & evidence

ORD record
ord-1e573491a3b7449e8ce69c6ab911b0f0
Source dataset
uspto-grants-2016_02
Patent number
US09259426B2

Reaction notes

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