5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine-7-carboxylic acid

Base Information

• Chemical Name: 5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine-7-carboxylic acid
• CAS No.: 492438-96-7
• Molecular Formula: C₂₃H₁₉N₇O₃
• Molecular Weight: 441.449

Synonyms:5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine-7-carboxylic acid

Chemical Property of 5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine-7-carboxylic acid

Chemical Property:

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Technology Process of 5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine-7-carboxylic acid

There total 13 articles about 5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine-7-carboxylic acid 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: 93.0%

guanidine hydrochloride (50-01-1) + 9-Benzylamino-5-((E)-3-dimethylamino-acryloyl)-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine-7-carboxylic acid ethyl ester → 5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine-7-carboxylic acid (492438-96-7)

Guidance literature:

With potassium carbonate; In 2-methoxy-ethanol; for 24h; Heating;

DOI:10.1021/jo026508x

Reference yield:

ethyl α-azido-β-(4-methoxypyrid-3-yl)acrylate (290332-96-6) → 5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine-7-carboxylic acid (492438-96-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 67 percent / o-xylene / 0.42 h / 170 °C

2.1: 94 percent / sodium hydride / dimethylformamide / 12 h / 20 °C

3.1: 93 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

4.1: 86 percent / MnO₂ / CH₂Cl₂ / 72 h / 20 °C

5.1: 85 percent / Na / ethanol / 72 h / -15 °C

6.1: 82 percent / CH₂Cl₂ / 24 h / 20 °C

7.1: 70 percent / Bu₄NF/SiO₂ / 0.03 h / microwave irradiation

8.1: 97 percent / tetrahydrofuran / 24 h / 50 °C

9.1: POCl₃ / CHCl₃ / 0.42 h / 20 °C

9.2: 90 percent / CHCl₃ / 30 h / 70 °C

10.1: 45 percent / dimethylformamide / 110 °C

11.1: 93 percent / K₂CO₃ / 2-methoxy-ethanol / 24 h / Heating

With manganese(IV) oxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium; silica gel; sodium hydride; potassium carbonate; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; chloroform; 2-methoxy-ethanol; o-xylene; N,N-dimethyl-formamide; 6.1: Staudinger reaction;

DOI:10.1021/jo026508x

Reference yield:

2-ethoxycarbonyl-4-methoxypyrrolo[2,3-b]pyridine (290332-97-7) → 5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine-7-carboxylic acid (492438-96-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 94 percent / sodium hydride / dimethylformamide / 12 h / 20 °C

2.1: 93 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

3.1: 86 percent / MnO₂ / CH₂Cl₂ / 72 h / 20 °C

4.1: 85 percent / Na / ethanol / 72 h / -15 °C

5.1: BF₃*OEt₂ / CH₂Cl₂ / 3 h / 20 °C

5.2: NaOH / CH₂Cl₂; H₂O / 3 h

6.1: 1.59 g / CH₂Cl₂ / 12 h / 20 °C

7.1: 97 percent / tetrahydrofuran / 24 h / 50 °C

8.1: POCl₃ / CHCl₃ / 0.42 h / 20 °C

8.2: 90 percent / CHCl₃ / 30 h / 70 °C

9.1: 45 percent / dimethylformamide / 110 °C

10.1: 93 percent / K₂CO₃ / 2-methoxy-ethanol / 24 h / Heating

With manganese(IV) oxide; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; sodium; sodium hydride; potassium carbonate; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; chloroform; 2-methoxy-ethanol; N,N-dimethyl-formamide; 6.1: Staudinger reaction;

DOI:10.1021/jo026508x

upstream raw materials:

guanidine hydrochloride

2-ethoxycarbonyl-4-methoxypyrrolo[2,3-b]pyridine

ethyl α-azido-β-(4-methoxypyrid-3-yl)acrylate

[4-methoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-methanol

Downstream raw materials:

5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-4-ol

[5-(2-Amino-pyrimidin-4-yl)-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-9-yl]-benzyl-amine

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