(1S,2R,3S,4R,5S)-4-(2-((3-fluorophenyl)ethynyl)-6-(methylamino)-9H-purin-9-yl)-2,3-O-isopropylidene-N-methylbicyclo[3.1.0]hexane-1-carboxamide

Base Information

Chemical Name:(1S,2R,3S,4R,5S)-4-(2-((3-fluorophenyl)ethynyl)-6-(methylamino)-9H-purin-9-yl)-2,3-O-isopropylidene-N-methylbicyclo[3.1.0]hexane-1-carboxamide
CAS No.:1377273-27-2
Molecular Formula:C₂₅H₂₅FN₆O₃
Molecular Weight:476.51
Hs Code.:

Synonyms:(1S,2R,3S,4R,5S)-4-(2-((3-fluorophenyl)ethynyl)-6-(methylamino)-9H-purin-9-yl)-2,3-O-isopropylidene-N-methylbicyclo[3.1.0]hexane-1-carboxamide

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Chemical Property of (1S,2R,3S,4R,5S)-4-(2-((3-fluorophenyl)ethynyl)-6-(methylamino)-9H-purin-9-yl)-2,3-O-isopropylidene-N-methylbicyclo[3.1.0]hexane-1-carboxamide

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Technology Process of (1S,2R,3S,4R,5S)-4-(2-((3-fluorophenyl)ethynyl)-6-(methylamino)-9H-purin-9-yl)-2,3-O-isopropylidene-N-methylbicyclo[3.1.0]hexane-1-carboxamide

There total 3 articles about (1S,2R,3S,4R,5S)-4-(2-((3-fluorophenyl)ethynyl)-6-(methylamino)-9H-purin-9-yl)-2,3-O-isopropylidene-N-methylbicyclo[3.1.0]hexane-1-carboxamide 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: 75.0%

: 2561-17-3
1-ethynyl-3-fluoro-benzene

: 1377273-17-0
(3aR,3bS,4aS,5R,5aS)-5-(2-iodo-6-(methylamino)-9H-purin-9-yl)-N,2,2-trimethyltetrahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxole-3b(3aH)-carboxamide

: 1377273-27-2
(1S,2R,3S,4R,5S)-4-(2-((3-fluorophenyl)ethynyl)-6-(methylamino)-9H-purin-9-yl)-2,3-O-isopropylidene-N-methylbicyclo[3.1.0]hexane-1-carboxamide

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/jm300396n

Reference yield:

: 793695-77-9
(1'S,2'R,3'S,4'R,5'S)-4'-[6-chloro-2-iodopurin-9-yl]-2',3'-isopropylidenebicyclo[3.1.0]hexane-1'-carboxylic acid ethyl ester

: 1377273-27-2
(1S,2R,3S,4R,5S)-4-(2-((3-fluorophenyl)ethynyl)-6-(methylamino)-9H-purin-9-yl)-2,3-O-isopropylidene-N-methylbicyclo[3.1.0]hexane-1-carboxamide

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine / methanol / 20 °C

2: methanol / 48 h / 20 °C

3: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In methanol; N,N-dimethyl-formamide; 3: Sonogashira coupling;
DOI:10.1021/jm300396n

Reference yield:

: 1377273-14-7
ethyl (3aR,3bS,4aS,5R,5aS)-5-(2-iodo-6-(methylamino)-9H-purin-9-yl)-2,2-dimethyltetrahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxole-3b(3aH)-carboxylate

: 1377273-27-2
(1S,2R,3S,4R,5S)-4-(2-((3-fluorophenyl)ethynyl)-6-(methylamino)-9H-purin-9-yl)-2,3-O-isopropylidene-N-methylbicyclo[3.1.0]hexane-1-carboxamide

Guidance literature:: Multi-step reaction with 2 steps

1: methanol / 48 h / 20 °C

2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In methanol; N,N-dimethyl-formamide; 2: Sonogashira coupling;
DOI:10.1021/jm300396n