1-[1-{[1-azido-3-(triphenylmethoxy)propan-2-yl]oxy}-2-(prop-2-yn-1-yloxy)ethyl]pyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-[1-{[1-azido-3-(triphenylmethoxy)propan-2-yl]oxy}-2-(prop-2-yn-1-yloxy)ethyl]pyrimidine-2,4(1H,3H)-dione
• CAS No.: 1610592-69-2
• Molecular Formula: C₃₁H₂₉N₅O₅
• Molecular Weight: 551.602

Synonyms:1-[1-{[1-azido-3-(triphenylmethoxy)propan-2-yl]oxy}-2-(prop-2-yn-1-yloxy)ethyl]pyrimidine-2,4(1H,3H)-dione

Chemical Property of 1-[1-{[1-azido-3-(triphenylmethoxy)propan-2-yl]oxy}-2-(prop-2-yn-1-yloxy)ethyl]pyrimidine-2,4(1H,3H)-dione

Chemical Property:

Purity/Quality:

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Technology Process of 1-[1-{[1-azido-3-(triphenylmethoxy)propan-2-yl]oxy}-2-(prop-2-yn-1-yloxy)ethyl]pyrimidine-2,4(1H,3H)-dione

There total 6 articles about 1-[1-{[1-azido-3-(triphenylmethoxy)propan-2-yl]oxy}-2-(prop-2-yn-1-yloxy)ethyl]pyrimidine-2,4(1H,3H)-dione 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: 88.0%

1-(1-{[1-azido-3-(triphenylmethoxy)propan-2-yl]oxy}-2-hydroxyethyl)pyrimidine-2,4(1H,3H)-dione (1610592-68-1) + propargyl bromide (106-96-7) → 1-[1-{[1-azido-3-(triphenylmethoxy)propan-2-yl]oxy}-2-(prop-2-yn-1-yloxy)ethyl]pyrimidine-2,4(1H,3H)-dione (1610592-69-2)

Guidance literature:

1-(1-{[1-azido-3-(triphenylmethoxy)propan-2-yl]oxy}-2-hydroxyethyl)pyrimidine-2,4(1H,3H)-dione; With sodium hydride; In tetrahydrofuran; for 0.5h; Inert atmosphere; Cooling with ice;

propargyl bromide; In tetrahydrofuran; at 20 ℃; for 0.833333h; Inert atmosphere; Sonication;

DOI:10.1002/hlca.201300289

Reference yield:

5'-O-trityluridine (6554-10-5) → 1-[1-{[1-azido-3-(triphenylmethoxy)propan-2-yl]oxy}-2-(prop-2-yn-1-yloxy)ethyl]pyrimidine-2,4(1H,3H)-dione (1610592-69-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium periodate / 1,4-dioxane; water / 2 h / 20 °C / Inert atmosphere; Darkness

2.1: sodium tetrahydroborate / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere

4.1: lithium azide / N,N-dimethyl-formamide / 3 h / 55 °C / Inert atmosphere

5.1: sodium hydroxide; water / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

6.1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice

6.2: 0.83 h / 20 °C / Inert atmosphere; Sonication

With sodium tetrahydroborate; sodium periodate; lithium azide; water; sodium hydride; triethylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/hlca.201300289

Reference yield:

1-(2-hydroxy-1-{[1-hydroxy-3-(triphenylmethoxy)propan-2-yl]oxy}ethyl)pyrimidine-2,4(1H,3H)-dione (101527-47-3) → 1-[1-{[1-azido-3-(triphenylmethoxy)propan-2-yl]oxy}-2-(prop-2-yn-1-yloxy)ethyl]pyrimidine-2,4(1H,3H)-dione (1610592-69-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere

2.1: lithium azide / N,N-dimethyl-formamide / 3 h / 55 °C / Inert atmosphere

3.1: sodium hydroxide; water / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice

4.2: 0.83 h / 20 °C / Inert atmosphere; Sonication

With lithium azide; water; sodium hydride; triethylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.201300289

upstream raw materials:

5'-O-trityluridine

1-(2-hydroxy-1-{[1-hydroxy-3-(triphenylmethoxy)propan-2-yl]oxy}ethyl)pyrimidine-2,4(1H,3H)-dione

2',3'-di-O-mesyl-5'-O-trityl-2',3'-seco-uridine

1-(1-{[1-azido-3-(triphenylmethoxy)propan-2-yl]oxy}-2-hydroxyethyl)pyrimidine-2,4(1H,3H)-dione

Downstream raw materials:

6,7,9,10-tetrahydro-1-{9-[(triphenylmethoxy)methyl]-4H-[1,2,3]triazolo[5,1-f][1,4,7]dioxazonin-7-yl}pyrimidine-2,4(1H,3H)-dione

4-amino-6,7,9,10-tetrahydro-1-{9-[(triphenylmethoxy)methyl]-4H-[1,2,3]triazolo[5,1-f][1,4,7]dioxazonin-7-yl}pyrimidin-2(1H)-one

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