4-{4-[4-(2-cyano-1-hydroxyethyl)-2,6-dimethylphenylamino]pyrimidin-2-ylamino}benzonitrile

Base Information

• Chemical Name: 4-{4-[4-(2-cyano-1-hydroxyethyl)-2,6-dimethylphenylamino]pyrimidin-2-ylamino}benzonitrile
• CAS No.: 500288-14-2
• Molecular Formula: C₂₂H₂₀N₆O
• Molecular Weight: 384.44

Synonyms:4-{4-[4-(2-cyano-1-hydroxyethyl)-2,6-dimethylphenylamino]pyrimidin-2-ylamino}benzonitrile

Chemical Property of 4-{4-[4-(2-cyano-1-hydroxyethyl)-2,6-dimethylphenylamino]pyrimidin-2-ylamino}benzonitrile

Chemical Property:

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Technology Process of 4-{4-[4-(2-cyano-1-hydroxyethyl)-2,6-dimethylphenylamino]pyrimidin-2-ylamino}benzonitrile

There total 5 articles about 4-{4-[4-(2-cyano-1-hydroxyethyl)-2,6-dimethylphenylamino]pyrimidin-2-ylamino}benzonitrile 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: 49.0%

acetonitrile (75-05-8,26809-02-9) + 4-[4-(4-formyl-2,6-dimethylphenylamino)pyrimidin-2-ylamino]benzonitrile (500293-29-8) → 4-{4-[4-(2-cyano-1-hydroxyethyl)-2,6-dimethylphenylamino]pyrimidin-2-ylamino}benzonitrile (500288-14-2)

Guidance literature:

acetonitrile; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -20 ℃; for 1h;

4-[4-(4-formyl-2,6-dimethylphenylamino)pyrimidin-2-ylamino]benzonitrile; In tetrahydrofuran; hexane; at -70 ℃; for 2h;

DOI:10.1021/jm040838n

Reference yield:

4-[4-(4-hydroxymethyl-2,6-dimethylphenylamino)pyrimidin-2-ylamino]benzonitrile (823786-21-6) → 4-{4-[4-(2-cyano-1-hydroxyethyl)-2,6-dimethylphenylamino]pyrimidin-2-ylamino}benzonitrile (500288-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 69 percent / MnO₂ / CH₂Cl₂ / 20 h / 20 °C

2.1: LDA / hexane; tetrahydrofuran / 1 h / -20 °C

2.2: 49 percent / hexane; tetrahydrofuran / 2 h / -70 °C

With manganese(IV) oxide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jm040838n

Reference yield:

4-amino-3,5-dimethylbenzoic acid ethyl ester (3095-47-4) → 4-{4-[4-(2-cyano-1-hydroxyethyl)-2,6-dimethylphenylamino]pyrimidin-2-ylamino}benzonitrile (500288-14-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93 percent / 2 h / 150 °C

2.1: 79 percent / LiAlH₄ / tetrahydrofuran / 0 - 20 °C

3.1: 69 percent / MnO₂ / CH₂Cl₂ / 20 h / 20 °C

4.1: LDA / hexane; tetrahydrofuran / 1 h / -20 °C

4.2: 49 percent / hexane; tetrahydrofuran / 2 h / -70 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jm040838n

upstream raw materials:

acetonitrile

4-[4-(4-formyl-2,6-dimethylphenylamino)pyrimidin-2-ylamino]benzonitrile

4-amino-3,5-dimethylbenzoic acid ethyl ester

4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile

Downstream raw materials:

4-{4-[4-(2-cyanoacetyl)-2,6-dimethylphenylamino]pyrimidin-2-ylamino}benzonitrile

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