5-(1-tert-Butyloxycarbonyl-2,3-dihydro-1H-indol-5-yl)-7-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine

Base Information

• Chemical Name: 5-(1-tert-Butyloxycarbonyl-2,3-dihydro-1H-indol-5-yl)-7-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine
• CAS No.: 1391053-27-2
• Molecular Formula: C₂₀H₂₃N₅O₂
• Molecular Weight: 365.435
• Hs Code.: 2933998090
• Mol file: 1391053-27-2.mol

Synonyms:

Chemical Property of 5-(1-tert-Butyloxycarbonyl-2,3-dihydro-1H-indol-5-yl)-7-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine

Chemical Property:

• Melting Point: 185-195°C (dec.)
• Boiling Point: 594.9±50.0 °C(Predicted)
• PKA: 5.76±0.30(Predicted)
• Density: 1.33±0.1 g/cm3(Predicted)
• Solubility.: DMSO (Slightly, Heated), Methanol (Very Slightly)

Purity/Quality:

99% ^*data from raw suppliers

5-(1-tert-Butyloxycarbonyl-2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Intermediate in the synthesis of GSK PERK Inhibitor (G797800).

Technology Process of 5-(1-tert-Butyloxycarbonyl-2,3-dihydro-1H-indol-5-yl)-7-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine

There total 10 articles about 5-(1-tert-Butyloxycarbonyl-2,3-dihydro-1H-indol-5-yl)-7-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine 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: 67.0%

1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indole-1-carboxylate (837392-67-3) + 5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (1337532-51-0) → 1,1-dimethylethyl 5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2,3-dihydro-1H-indole-1-carboxylate (1391053-27-2)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; potassium phosphate monohydrate; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; water; at 85 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/jm300713s

Reference yield: 58.0%

4-amino-5-iodo-7-methylpyrrolo[2,3‐d]pyrimidine (862729-13-3) + 1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indole-1-carboxylate (837392-67-3) → 1,1-dimethylethyl 5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2,3-dihydro-1H-indole-1-carboxylate (1391053-27-2)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate; tricyclohexylphosphine; In 1,4-dioxane; water; at 95 ℃; for 18h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.8b01652

Reference yield:

5-bromoindoline (22190-33-6) → 1,1-dimethylethyl 5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2,3-dihydro-1H-indole-1-carboxylate (1391053-27-2)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap / acetonitrile / 3 h / 20 °C

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere

3: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; potassium phosphate monohydrate; tri tert-butylphosphoniumtetrafluoroborate / 1,4-dioxane; water / 1.5 h / 85 °C / Inert atmosphere

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate monohydrate; potassium acetate; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; water; acetonitrile;

DOI:10.1021/jm300713s

upstream raw materials:

1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indole-1-carboxylate

5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

5-bromoindoline

Downstream raw materials:

5-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

5-{1-[(2-fluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

5-{1-[(3-fluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

5-{1-[(4-fluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

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