6-(4-chloropyridin-2-yl)-7-((trans-4-methylcyclohexyl)methyl)-7H-purine-2-carbonitrile

Base Information

• Chemical Name: 6-(4-chloropyridin-2-yl)-7-((trans-4-methylcyclohexyl)methyl)-7H-purine-2-carbonitrile
• CAS No.: 1621912-03-5
• Molecular Formula: C₁₉H₁₉ClN₆
• Molecular Weight: 366.853
• Mol file: 1621912-03-5.mol

Synonyms:6-(4-chloropyridin-2-yl)-7-((trans-4-methylcyclohexyl)methyl)-7H-purine-2-carbonitrile

Chemical Property of 6-(4-chloropyridin-2-yl)-7-((trans-4-methylcyclohexyl)methyl)-7H-purine-2-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(4-chloropyridin-2-yl)-7-((trans-4-methylcyclohexyl)methyl)-7H-purine-2-carbonitrile

There total 9 articles about 6-(4-chloropyridin-2-yl)-7-((trans-4-methylcyclohexyl)methyl)-7H-purine-2-carbonitrile 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:

4-chloro-2-(tributylstannyl)pyridine (1204580-71-1) + 6-chloro-7-((trans-4-methylcyclohexyl)methyl)-7H-purine-2-carbonitrile (1621911-92-9) → 6-(4-chloropyridin-2-yl)-7-((trans-4-methylcyclohexyl)methyl)-7H-purine-2-carbonitrile (1621912-03-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 110 ℃; for 14h; Sealed tube; Inert atmosphere;

Reference yield:

trans-4-methylcyclohexanecarboxylic acid (934-67-8,4331-54-8,13064-83-0) → 6-(4-chloropyridin-2-yl)-7-((trans-4-methylcyclohexyl)methyl)-7H-purine-2-carbonitrile (1621912-03-5)

Guidance literature:

Multi-step reaction with 9 steps

1: diborane / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C

3: sodium carbonate / N,N-dimethyl-formamide; dimethyl sulfoxide / 24 h / 100 °C

4: trichlorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene / 5 h / 60 - 120 °C

5: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 85 °C

6: bis(η3-allyl-μ-chloropalladium(II)); XPhos / N,N-dimethyl acetamide / 2 h / 120 °C / Inert atmosphere

7: trifluoroacetic acid / neat (no solvent) / 6 h / 20 °C

8: magnesium sulfate; copper dichloride; tert.-butylnitrite / acetonitrile / 1 h / 20 - 70 °C

9: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 14 h / 110 °C / Sealed tube; Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; tert.-butylnitrite; bis(η3-allyl-μ-chloropalladium(II)); carbon tetrabromide; sodium carbonate; magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; copper dichloride; diborane; XPhos; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl acetamide; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 9: |Stille Cross Coupling;

Reference yield:

(trans-4-methylcyclohexyl)methanol (3937-49-3) → 6-(4-chloropyridin-2-yl)-7-((trans-4-methylcyclohexyl)methyl)-7H-purine-2-carbonitrile (1621912-03-5)

Guidance literature:

Multi-step reaction with 8 steps

1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C

2: sodium carbonate / N,N-dimethyl-formamide; dimethyl sulfoxide / 24 h / 100 °C

3: trichlorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene / 5 h / 60 - 120 °C

4: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 85 °C

5: bis(η3-allyl-μ-chloropalladium(II)); XPhos / N,N-dimethyl acetamide / 2 h / 120 °C / Inert atmosphere

6: trifluoroacetic acid / neat (no solvent) / 6 h / 20 °C

7: magnesium sulfate; copper dichloride; tert.-butylnitrite / acetonitrile / 1 h / 20 - 70 °C

8: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 14 h / 110 °C / Sealed tube; Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; tert.-butylnitrite; bis(η3-allyl-μ-chloropalladium(II)); carbon tetrabromide; sodium carbonate; magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; copper dichloride; XPhos; trichlorophosphate; In 1,4-dioxane; dichloromethane; N,N-dimethyl acetamide; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 8: |Stille Cross Coupling;

upstream raw materials:

4-chloro-2-(tributylstannyl)pyridine

6-chloro-7-((trans-4-methylcyclohexyl)methyl)-7H-purine-2-carbonitrile

trans-4-methylcyclohexanecarboxylic acid

(trans-4-methylcyclohexyl)methanol

Downstream raw materials:

6-(4-chloropyridin-2-yl)-N-hydroxy-7-(((trans)-4-methylcyclohexyl)methyl)-7H-purine-2-carboximidamide

3-{6-(4-chloropyridin-2-yl)-7-[(trans-4-methylcyclohexyl)methyl]-7H-purin-2-yl}-1,2,4-oxadiazol-5(4H)-one

Refernces