N-[4-((1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-bicyclo[3.1.0]hex-1-ylamino)-6-chloro-pyrimidin-5-yl]-formamide

Base Information

• Chemical Name: N-[4-((1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-bicyclo[3.1.0]hex-1-ylamino)-6-chloro-pyrimidin-5-yl]-formamide
• CAS No.: 190195-83-6
• Molecular Formula: C₂₆H₂₇ClN₄O₃
• Molecular Weight: 478.978
• Mol file: 190195-83-6.mol

Synonyms:N-[4-((1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-bicyclo[3.1.0]hex-1-ylamino)-6-chloro-pyrimidin-5-yl]-formamide

Chemical Property of N-[4-((1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-bicyclo[3.1.0]hex-1-ylamino)-6-chloro-pyrimidin-5-yl]-formamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[4-((1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-bicyclo[3.1.0]hex-1-ylamino)-6-chloro-pyrimidin-5-yl]-formamide

There total 9 articles about N-[4-((1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-bicyclo[3.1.0]hex-1-ylamino)-6-chloro-pyrimidin-5-yl]-formamide 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: 92.0%

4,6-dichloro-5-formamidopyrimidine (123240-66-4) + (1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-aminobicyclo<3.1.0>hexane (170453-02-8) → N-[4-((1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-bicyclo[3.1.0]hex-1-ylamino)-6-chloro-pyrimidin-5-yl]-formamide (190195-83-6)

Guidance literature:

With triethylamine; In 1,4-dioxane; for 24h; Heating;

DOI:10.1039/a604352f

Reference yield:

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane (110567-22-1) → N-[4-((1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-bicyclo[3.1.0]hex-1-ylamino)-6-chloro-pyrimidin-5-yl]-formamide (190195-83-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 77.5 percent / LiClO₄ / acetonitrile / 96 h / 70 °C

2: 98 percent / 1,1'-thiocarbonyldiimidazole, DMAP / dimethylformamide / 1.) r.t., 3 h, 2.) 70 deg C, 30 min

3: 96.5 percent / CHCl₃; diethyl ether / 72 h / 0 °C

4: benzophenone / benzene; acetonitrile / 2 h / Irradiation

5: 25percent aq. NaOH / methanol / 24 h / Heating

6: Et₃N, DPPA / toluene / 1.) r.t., 2 h, 2.) 80 deg C, 2 h

7: toluene / 1.) 80 deg C, 2 h, 2.) r.t., overnight

8: 99 percent / Bu₄NF / acetonitrile; tetrahydrofuran / 4 h / 70 °C

9: 92 percent / Et₃N / dioxane / 24 h / Heating

With dmap; sodium hydroxide; benzophenone; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; lithium perchlorate; triethylamine; 1,1'-Thiocarbonyldiimidazole; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1039/a604352f

Reference yield:

(3R,4S)-1-Cyano-4-benzyloxy-3-benzyloxymethylcyclopentene (170452-98-9) → N-[4-((1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-bicyclo[3.1.0]hex-1-ylamino)-6-chloro-pyrimidin-5-yl]-formamide (190195-83-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 96.5 percent / CHCl₃; diethyl ether / 72 h / 0 °C

2: benzophenone / benzene; acetonitrile / 2 h / Irradiation

3: 25percent aq. NaOH / methanol / 24 h / Heating

4: Et₃N, DPPA / toluene / 1.) r.t., 2 h, 2.) 80 deg C, 2 h

5: toluene / 1.) 80 deg C, 2 h, 2.) r.t., overnight

6: 99 percent / Bu₄NF / acetonitrile; tetrahydrofuran / 4 h / 70 °C

7: 92 percent / Et₃N / dioxane / 24 h / Heating

With sodium hydroxide; benzophenone; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; chloroform; toluene; acetonitrile; benzene;

DOI:10.1039/a604352f

upstream raw materials:

4,6-dichloro-5-formamidopyrimidine

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-aminobicyclo<3.1.0>hexane

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

(3R,4S)-1-Cyano-4-benzyloxy-3-benzyloxymethylcyclopentene

Downstream raw materials:

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-(6-aminopurin-9-yl)bicyclo[3.1.0]hexane

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-(6-chloropurin-9-yl)bicyclo[3.1.0]hexane