[¹⁸F]-N,N-diethyl-2-(2-(4-(5-fluoropent-1-yn-1-yl)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide

Base Information

• Chemical Name: [¹⁸F]-N,N-diethyl-2-(2-(4-(5-fluoropent-1-yn-1-yl)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide
• CAS No.: 1580494-77-4
• Molecular Formula: C₂₅H₂₉FN₄O
• Molecular Weight: 419.531

Synonyms:[¹⁸F]-N,N-diethyl-2-(2-(4-(5-fluoropent-1-yn-1-yl)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide

Chemical Property of [¹⁸F]-N,N-diethyl-2-(2-(4-(5-fluoropent-1-yn-1-yl)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide

Chemical Property:

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Technology Process of [¹⁸F]-N,N-diethyl-2-(2-(4-(5-fluoropent-1-yn-1-yl)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide

There total 7 articles about [¹⁸F]-N,N-diethyl-2-(2-(4-(5-fluoropent-1-yn-1-yl)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide 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:

5-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl)phenyl)pent-4-yn-1-yl 4-methylbenzenesulfonate (1580494-73-0) → [18F]-N,N-diethyl-2-(2-(4-(5-fluoropent-1-yn-1-yl)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide (1580494-77-4)

Guidance literature:

With K[18F]F-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane complex; potassium carbonate; In dimethyl sulfoxide; at 100 ℃; for 0.166667h;

DOI:10.1016/j.bmcl.2014.01.080

Reference yield:

N,N-diethyl-2-(2-(4-(5-hydroxypent-1-yn-1-yl)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide (1580494-27-4) → [18F]-N,N-diethyl-2-(2-(4-(5-fluoropent-1-yn-1-yl)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide (1580494-77-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: K[18F]F-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane complex; potassium carbonate / dimethyl sulfoxide / 0.17 h / 100 °C

With K[18F]F-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane complex; potassium carbonate; triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.bmcl.2014.01.080

Reference yield:

methyl 4-iodobenzoate (619-44-3) → [18F]-N,N-diethyl-2-(2-(4-(5-fluoropent-1-yn-1-yl)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide (1580494-77-4)

Guidance literature:

Multi-step reaction with 7 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

7.1: K[18F]F-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane complex; potassium carbonate / dimethyl sulfoxide / 0.17 h / 100 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; K[18F]F-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane complex; potassium carbonate; hydrazine hydrate; acetic acid; diethylamine; triethylamine; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; 5.1: |Sonogashira Cross-Coupling;

DOI:10.1016/j.bmcl.2014.01.080

upstream raw materials:

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

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

methyl 4-iodobenzoate

3-(4-iodophenyl)-3-oxopropanenitrile

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