N⁸-cyclopropylmethyl-N²-(2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]pyrimidine-2,8-diamine

Base Information

• Chemical Name: N⁸-cyclopropylmethyl-N²-(2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]pyrimidine-2,8-diamine
• CAS No.: 1578244-15-1
• Molecular Formula: C₂₂H₂₃N₇O
• Molecular Weight: 401.471

Synonyms:N⁸-cyclopropylmethyl-N²-(2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]pyrimidine-2,8-diamine

Chemical Property of N⁸-cyclopropylmethyl-N²-(2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]pyrimidine-2,8-diamine

Chemical Property:

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Technology Process of N⁸-cyclopropylmethyl-N²-(2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]pyrimidine-2,8-diamine

There total 8 articles about N⁸-cyclopropylmethyl-N²-(2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]pyrimidine-2,8-diamine 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: 63.0%

8-chloro-N-(2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]-pyrimidin-2-amine (1578244-55-9) + cyclopropanemethylamine (2516-47-4) → N8-cyclopropylmethyl-N2-(2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]pyrimidine-2,8-diamine (1578244-15-1)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 130 ℃; for 7h; Sealed tube;

DOI:10.1021/acs.jmedchem.5b01811

Reference yield:

8-chloro-2-(methylsulfonyl)pyrido[3,4-d]pyrimidine (1578246-63-5) → N8-cyclopropylmethyl-N2-(2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]pyrimidine-2,8-diamine (1578244-15-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 - 20 °C

1.2: 18 h / 0 - 20 °C

1.3: 1 h

2.1: 1-methyl-pyrrolidin-2-one / 7 h / 130 °C

With sodium hydride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one;

Reference yield:

5-bromo-2-methylsulfanyl-pyrimidine-4-carboxylic acid (50593-92-5) → N8-cyclopropylmethyl-N2-(2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]pyrimidine-2,8-diamine (1578244-15-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sulfuric acid / 24 h / Reflux

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / water; tetrahydrofuran / 18 h / 65 °C

3.1: ammonia / methanol / 18 h / 85 °C

3.2: 2 h / 90 °C

4.1: trichlorophosphate / 18 h / 70 °C

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 18 h / 0 - 20 °C

6.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 - 20 °C

6.2: 18 h / 0 - 20 °C

6.3: 1 h

7.1: 1-methyl-pyrrolidin-2-one / 7 h / 130 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sulfuric acid; ammonia; sodium hydride; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water;

upstream raw materials:

8-chloro-N-(2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]-pyrimidin-2-amine

cyclopropanemethylamine

8-chloro-2-(methylsulfonyl)pyrido[3,4-d]pyrimidine

5-bromo-2-methylsulfanyl-pyrimidine-4-carboxylic acid

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