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177417-73-1

1H-Imidazole-2,4-dicarboxylic acid, 4-(1,1-dimethylethyl) 2-ethyl ester synthesis

2synthesis methods
13831-03-3 Synthesis
TERT-BUTYL PROPIOLATE

13831-03-3
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Acetic acid, 2-amino-2-(hydroxyimino)-, ethyl ester, (2E)-

1217428-98-2
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1H-Imidazole-2,4-dicarboxylic acid, 4-(1,1-dimethylethyl) 2-ethyl ester

177417-73-1
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-

Yield:-

Reaction Conditions:

with triethylamine

Steps:

260 Example 260

Example 260
Synthesis of 4-(tert-butyl) 2-ethyl 1H-imidazole-2,4-dicarboxylate.
To a mixture of ethyl (Z)-2-amino-2-(hydroxyimino)acetate (660 mg, 5 mmol) and tert-butyl propiolate (694 mg, 5.5 mmol) in Xylene (10 mL) was added TEA (606 mg, 6 mmol).
The mixture was stirred at 140° C. for 16 h.
After cooled to RT, H2O (25 mL) was added and the mixture was extracted with EtOAc (35 mL*3).
The combined organic layers were washed with brine and dried over Na2SO4, concentrated to give the crude, which was purified by silica gel chromatography (PE/EA=1/1) to give 4-(tert-butyl) 2-ethyl 1H-imidazole-2,4-dicarboxylate (400 mg, yield: 33%) as a yellow solid. ESI-MS [M+H]+: 241.1.

References:

US2019/284182,2019,A1