1-(4-(7-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-methyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)-3-ethylurea

Base Information

• Chemical Name: 1-(4-(7-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-methyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)-3-ethylurea
• CAS No.: 1285500-14-2
• Molecular Formula: C₂₀H₂₃N₇O₂
• Molecular Weight: 393.448
• Mol file: 1285500-14-2.mol

Synonyms:1-(4-(7-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-methyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)-3-ethylurea

Chemical Property of 1-(4-(7-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-methyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)-3-ethylurea

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(4-(7-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-methyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)-3-ethylurea

There total 6 articles about 1-(4-(7-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-methyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)-3-ethylurea 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:

1-ethyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]urea (874291-00-6) + (1S,4S)-5-(5-chloro-1-methyl-1H-pyrazolo[4,3-d]-pyrimidin-7-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (1285500-06-2) → 1-(4-(7-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-methyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)-3-ethylurea (1285500-14-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; sodium carbonate; In acetonitrile; at 120 ℃; for 0.25h; Microwave irradiation; Inert atmosphere;

DOI:10.1016/j.bmcl.2013.07.027

Reference yield:

4-amino-1-methyl-1H-pyrazole-5-carboxamide (92534-73-1) → 1-(4-(7-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-methyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)-3-ethylurea (1285500-14-2)

Guidance literature:

Multi-step reaction with 4 steps

1: acetonitrile / 19 h / 100 °C / Inert atmosphere; Reflux

2: trichlorophosphate; N,N-diethylaniline / 18 h / 130 °C / Inert atmosphere

3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; potassium acetate / acetonitrile / 0.25 h / 120 °C / Microwave irradiation; Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; sodium carbonate; N-ethyl-N,N-diisopropylamine; N,N-diethylaniline; trichlorophosphate; In N,N-dimethyl-formamide; acetonitrile; 4: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2013.07.027

Reference yield:

1-methyl-1H-pyrazolo[4,3-d]pyrimidine-5,7-(4H,6H)-dione (83824-38-8) → 1-(4-(7-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-methyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)-3-ethylurea (1285500-14-2)

Guidance literature:

Multi-step reaction with 3 steps

1: trichlorophosphate; N,N-diethylaniline / 18 h / 130 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; potassium acetate / acetonitrile / 0.25 h / 120 °C / Microwave irradiation; Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; sodium carbonate; N-ethyl-N,N-diisopropylamine; N,N-diethylaniline; trichlorophosphate; In N,N-dimethyl-formamide; acetonitrile; 3: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2013.07.027

upstream raw materials:

1-methyl-1H-pyrazole-5-carboxylic acid

4-amino-1-methyl-1H-pyrazole-5-carboxamide

1-methyl-1H-pyrazolo[4,3-d]pyrimidine-5,7-(4H,6H)-dione

5,7-dichloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine