4-(4-fluoro-2-methylphenyl)-2-methanesulfonyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Base Information

• Chemical Name: 4-(4-fluoro-2-methylphenyl)-2-methanesulfonyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• CAS No.: 950661-98-0
• Molecular Formula: C₂₁H₂₅FN₄O₃SSi
• Molecular Weight: 460.604

Synonyms:4-(4-fluoro-2-methylphenyl)-2-methanesulfonyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Chemical Property of 4-(4-fluoro-2-methylphenyl)-2-methanesulfonyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Chemical Property:

Purity/Quality:

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Technology Process of 4-(4-fluoro-2-methylphenyl)-2-methanesulfonyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

There total 9 articles about 4-(4-fluoro-2-methylphenyl)-2-methanesulfonyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-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: 92.0%

4-(4-?uoro-2-methylphenyl)-2-methylsulfanyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (950661-76-4) → 4-(4-fluoro-2-methylphenyl)-2-methanesulfonyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (950661-98-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.bmc.2012.08.050

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 4-(4-fluoro-2-methylphenyl)-2-methanesulfonyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (950661-98-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C

2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / -78 - 20 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.03 h / -78 °C

3.2: -78 - 20 °C

4.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 0.17 h

4.2: 0.25 h / 20 °C

5.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate / N,N-dimethyl-formamide; water / 3 h / 80 °C / Inert atmosphere

6.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 0 - 20 °C

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 20 °C

With bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; sodium hydride; sodium hydrogencarbonate; triethylamine; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 5.1: |Suzuki Coupling;

DOI:10.1016/j.bmc.2012.08.050

Reference yield:

4-chloro-2-methylsulfanyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine (950661-64-0) → 4-(4-fluoro-2-methylphenyl)-2-methanesulfonyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (950661-98-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / -78 - 20 °C

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.03 h / -78 °C

2.2: -78 - 20 °C

3.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 0.17 h

3.2: 0.25 h / 20 °C

4.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate / N,N-dimethyl-formamide; water / 3 h / 80 °C / Inert atmosphere

5.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 0 - 20 °C

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 20 °C

With bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; sodium hydrogencarbonate; triethylamine; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; 4.1: |Suzuki Coupling;

DOI:10.1016/j.bmc.2012.08.050

upstream raw materials:

4-(4-?uoro-2-methylphenyl)-2-methylsulfanyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

4-(4-fluoro-2-methylphenyl)-2-methylsulfanyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid amide

(2-trimethylethylsilylethoxy)methyl chloride

4-chloro-2-methylsulfanyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine

Downstream raw materials:

4-(4-fluoro-2-methyl-phenyl)-2-(4-methyl-piperazin-1-yl)-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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