1,1-dimethylethyl methyl[(3-{[5-(1-methylethenyl)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}phenyl)sulfonyl]carbamate

Base Information

• Chemical Name: 1,1-dimethylethyl methyl[(3-{[5-(1-methylethenyl)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}phenyl)sulfonyl]carbamate
• CAS No.: 1351094-66-0
• Molecular Formula: C₂₁H₂₅N₅O₄S
• Molecular Weight: 443.527
• Mol file: 1351094-66-0.mol

Synonyms:1,1-dimethylethyl methyl[(3-{[5-(1-methylethenyl)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}phenyl)sulfonyl]carbamate

Chemical Property of 1,1-dimethylethyl methyl[(3-{[5-(1-methylethenyl)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}phenyl)sulfonyl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1-dimethylethyl methyl[(3-{[5-(1-methylethenyl)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}phenyl)sulfonyl]carbamate

There total 5 articles about 1,1-dimethylethyl methyl[(3-{[5-(1-methylethenyl)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}phenyl)sulfonyl]carbamate 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: 17.0%

1,1-dimethylethyl 5-bromo-4-[(3-{[{[(1,1-dimethylethyl)oxy]carbonyl}(methyl)amino]sulfonyl}phenyl)amino]-7H-pyrrolo[2,3-d]pyrimidine-7-carboxylate (1351094-63-7) + 2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (126726-62-3) → 1,1-dimethylethyl methyl[(3-{[5-(1-methylethenyl)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}phenyl)sulfonyl]carbamate (1351094-66-0)

Guidance literature:

With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In water; at 100 ℃; for 0.25h; Inert atmosphere;

Reference yield:

3-[(5-bromo-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-N-methylbenzenesulfonamide trifluoroacetate → 1,1-dimethylethyl methyl[(3-{[5-(1-methylethenyl)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}phenyl)sulfonyl]carbamate (1351094-66-0)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap / acetonitrile / 0.25 h / 25 °C

2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water / 0.25 h / 100 °C / Inert atmosphere

With sodium carbonate; dmap; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In water; acetonitrile;

Reference yield:

5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (22276-95-5) → 1,1-dimethylethyl methyl[(3-{[5-(1-methylethenyl)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}phenyl)sulfonyl]carbamate (1351094-66-0)

Guidance literature:

Multi-step reaction with 3 steps

1: isopropyl alcohol / Heating

2: dmap / acetonitrile / 0.25 h / 25 °C

3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / water; 1,4-dioxane / 0.25 h / 100 °C / Inert atmosphere

With dmap; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; In 1,4-dioxane; water; isopropyl alcohol; acetonitrile;

DOI:10.1021/acs.jmedchem.5b00931

upstream raw materials:

1,1-dimethylethyl 5-bromo-4-[(3-{[{[(1,1-dimethylethyl)oxy]carbonyl}(methyl)amino]sulfonyl}phenyl)amino]-7H-pyrrolo[2,3-d]pyrimidine-7-carboxylate

2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

3-amino-N-methylbenzenesulfonamide

Downstream raw materials:

tert-butyl (3-((5-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)phenyl)sulfonyl(methyl)carbamate

Refernces

• 1、 -. "COMPOUNDS AND METHODS". Page/Page column 171-172. . Retrieved 2011/12/14.