5-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl)phenyl)pent-4-yn-1-yl 4-methylbenzenesulfonate

Base Information

Chemical Name:5-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl)phenyl)pent-4-yn-1-yl 4-methylbenzenesulfonate
CAS No.:1580494-73-0
Molecular Formula:C₃₂H₃₆N₄O₄S
Molecular Weight:572.728
Hs Code.:

Synonyms:5-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl)phenyl)pent-4-yn-1-yl 4-methylbenzenesulfonate

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Chemical Property of 5-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl)phenyl)pent-4-yn-1-yl 4-methylbenzenesulfonate

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Technology Process of 5-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl)phenyl)pent-4-yn-1-yl 4-methylbenzenesulfonate

There total 7 articles about 5-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl)phenyl)pent-4-yn-1-yl 4-methylbenzenesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 55.0%

: 4124-41-8
p-toluenesulfonylanhydride

: 1580494-27-4
N,N-diethyl-2-(2-(4-(5-hydroxypent-1-yn-1-yl)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide

: 1580494-73-0
5-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl)phenyl)pent-4-yn-1-yl 4-methylbenzenesulfonate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; for 5h;
DOI:10.1021/acs.jmedchem.5b00932

Reference yield:

: 619-44-3
methyl 4-iodobenzoate

: 1580494-73-0
5-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl)phenyl)pent-4-yn-1-yl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -65 °C

1.2: 2 h / -65 - -45 °C

2.1: sodium hydroxide / ethanol / 0.25 h

2.2: 96 h / 20 °C

3.1: hydrazine hydrate; acetic acid / ethanol / 80 °C

4.1: ethanol / 5 h / 80 °C

5.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / 24 h / 20 °C

6.1: triethylamine / dichloromethane / 3 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; hydrazine hydrate; acetic acid; diethylamine; triethylamine; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; 5.1: |Sonogashira Cross-Coupling;
DOI:10.1016/j.bmcl.2014.01.080

Reference yield:

: 206346-33-0
3-(4-iodophenyl)-3-oxopropanenitrile

: 1580494-73-0
5-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl)phenyl)pent-4-yn-1-yl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydroxide / ethanol / 0.25 h

1.2: 96 h / 20 °C

2.1: hydrazine hydrate; acetic acid / ethanol / 80 °C

3.1: ethanol / 5 h / 80 °C

4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / 24 h / 20 °C

5.1: triethylamine / dichloromethane / 3 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; hydrazine hydrate; acetic acid; diethylamine; triethylamine; sodium hydroxide; In ethanol; dichloromethane; 4.1: |Sonogashira Cross-Coupling;
DOI:10.1016/j.bmcl.2014.01.080