(R)-tert-butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl-6-d₁)-piperidine-1-carboxylate

Base Information

• Chemical Name: (R)-tert-butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl-6-d₁)-piperidine-1-carboxylate
• CAS No.: 1553977-58-4
• Molecular Formula: C₂₇H₃₀N₆O₃
• Molecular Weight: 487.566

Synonyms:(R)-tert-butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl-6-d₁)-piperidine-1-carboxylate

Chemical Property of (R)-tert-butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl-6-d₁)-piperidine-1-carboxylate

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Technology Process of (R)-tert-butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl-6-d₁)-piperidine-1-carboxylate

There total 4 articles about (R)-tert-butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl-6-d₁)-piperidine-1-carboxylate 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: 12.0%

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine-6-d1 (1553977-55-1) + tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate (143900-44-1) → (R)-tert-butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl-6-d1)-piperidine-1-carboxylate (1553977-58-4)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃;

Reference yield:

3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine-6-d1 (1553977-51-7) → (R)-tert-butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl-6-d1)-piperidine-1-carboxylate (1553977-58-4)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium phosphate monohydrate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 30 h / Inert atmosphere; Reflux

2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium phosphate monohydrate; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; water;

Reference yield:

4-Aminopyrazolo<3,4-d>pyrimidin (2380-63-4) → (R)-tert-butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl-6-d1)-piperidine-1-carboxylate (1553977-58-4)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium 10% on activated carbon; hydrogen; water-d2 / 32.5 h / 20 - 140 °C / 1034.32 Torr

2: N-iodo-succinimide / N,N-dimethyl-formamide / 4 h / 80 °C

3: potassium phosphate monohydrate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 30 h / Inert atmosphere; Reflux

4: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C

With N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium phosphate monohydrate; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen; water-d2; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;

upstream raw materials:

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine-6-d₁

tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate

1H-pyrazolo[3,4-d]pyrimidin-4-amine-3,6-d₂

3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine-6-d₁

Downstream raw materials:

(R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl-6-d₁)piperidin-1-yl)prop-2-en-1-one

(R)-3-(4-phenoxyphenyl)-1-(piperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine-6-d₁ hydrochloride

(R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl-6-d₁)piperidin-1-yl)prop-2-en-2,3,3-d₃-1-one

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