9H-Pyrimido[4,5-b]indole synthesis

5synthesis methods

Product Name:9H-Pyrimido[4,5-b]indole
CAS Number:5059-31-4
Molecular formula:C10H7N3
Molecular Weight:169.18

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Yield: 37.9%

Reaction Conditions:

with tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex;4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;sodium t-butanolate in 1,4-dioxane at 110; for 24 h;Inert atmosphere;

Steps:

9H-Pyrimido[4,5-b]indole (Intermediate S)
A mixture of 5-bromopyrimidin-4-amine (1 g, 5.78 mmol), iodobenzene (1.18 g, 5.78 mmol), xantphos (334 mg, 0.578 mmol), sodium tert-butoxide (1.66 g, 17.34 mmol) and tris(dibenzylideneacetone)dipalladium (0) (0.52 g, 0.58 mmol) in dioxane was degassed with nitrogen, heated to 110° C. and stirred for 24 hours. The reaction was cooled to r.t, poured into water and extracted with EtOAc (3×100 mL). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by flash chromatography (EtOAc/DCM=80%) to give 9H-pyrimido[4,5-b]indole (370 mg, 37.9% yield) as a yellow solid. LC/MS (ESI, m/z): [M+1]⁺=170.0.

References:

Kymera Therapeutics, Inc.;Ji, Nan;Kluge, Arthur F.;Weiss, Matthew M.;Zhang, Yi US2020/10468, 2020, A1 Location in patent:Paragraph 0762; 0763