(2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile

Base Information

Chemical Name:(2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile
CAS No.:750644-54-3
Molecular Formula:C₂₀H₂₀N₆O₄
Molecular Weight:408.417
Hs Code.:

Synonyms:(2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile

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Chemical Property of (2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile

Chemical Property:

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Technology Process of (2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile

There total 3 articles about (2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile 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: 15.0%

: 1986-47-6,2208-35-7,2337-86-2,4548-34-9,37388-05-9,54779-58-7,61-81-4
tranylcypromine hydrochloride

: 333333-74-7
(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate

: 750644-54-3
(2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile

Guidance literature:: tranylcypromine hydrochloride; (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 26h;

With sodium hydroxide; In water; acetonitrile; at 20 ℃; for 4h;
DOI:10.1016/j.bmc.2004.03.031

Reference yield:

: 2004-07-1
2-Amino-6-chloropurine riboside

: 750644-54-3
(2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile

Guidance literature:: Multi-step reaction with 4 steps

1.1: 89 percent / pyridine / dimethylformamide / 2 h / 80 °C

2.1: 69 percent / t-butyl nitrite; CH₂I₂ / acetonitrile / 3 h / 80 °C

3.1: 59 percent / Pd₂(dba)3-CHCl₃; tri-furylphosphine; tetramethylurea / 22 h / 80 °C

4.1: iPr₂NEt / dimethylformamide / 26 h / 20 °C

4.2: 15 percent / NaOH / acetonitrile; H₂O / 4 h / 20 °C

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tert.-butylnitrite; trifuran-2-yl-phosphane; diiodomethane; N-ethyl-N,N-diisopropylamine; tetramethylurea; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.bmc.2004.03.031

Reference yield:

: 16321-99-6
2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine

: 750644-54-3
(2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: 69 percent / t-butyl nitrite; CH₂I₂ / acetonitrile / 3 h / 80 °C

2.1: 59 percent / Pd₂(dba)3-CHCl₃; tri-furylphosphine; tetramethylurea / 22 h / 80 °C

3.1: iPr₂NEt / dimethylformamide / 26 h / 20 °C

3.2: 15 percent / NaOH / acetonitrile; H₂O / 4 h / 20 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tert.-butylnitrite; trifuran-2-yl-phosphane; diiodomethane; N-ethyl-N,N-diisopropylamine; tetramethylurea; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.bmc.2004.03.031