tert-butyl [5-(benzyloxy)-4-(di-tert-butylaminodicarbonate)-1,2-dihydro-1-(3,4-dihydroxybutyl)-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate

Base Information

• Chemical Name: tert-butyl [5-(benzyloxy)-4-(di-tert-butylaminodicarbonate)-1,2-dihydro-1-(3,4-dihydroxybutyl)-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate
• CAS No.: 1268383-27-2
• Molecular Formula: C₃₃H₄₆N₆O₁₀
• Molecular Weight: 686.762
• Mol file: 1268383-27-2.mol

Synonyms:tert-butyl [5-(benzyloxy)-4-(di-tert-butylaminodicarbonate)-1,2-dihydro-1-(3,4-dihydroxybutyl)-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate

Chemical Property of tert-butyl [5-(benzyloxy)-4-(di-tert-butylaminodicarbonate)-1,2-dihydro-1-(3,4-dihydroxybutyl)-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl [5-(benzyloxy)-4-(di-tert-butylaminodicarbonate)-1,2-dihydro-1-(3,4-dihydroxybutyl)-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate

There total 10 articles about tert-butyl [5-(benzyloxy)-4-(di-tert-butylaminodicarbonate)-1,2-dihydro-1-(3,4-dihydroxybutyl)-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate 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: 77.0%

tert-butyl [5-(benzyloxy)-1-(but-3-enyl)-4-(di-tert-butylaminodicarbonate)-1,2-dihydro-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate (1268383-26-1) → tert-butyl [5-(benzyloxy)-4-(di-tert-butylaminodicarbonate)-1,2-dihydro-1-(3,4-dihydroxybutyl)-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate (1268383-27-2)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 ℃;

DOI:10.1016/j.tetlet.2010.11.122

Reference yield:

4-(but-3-enylamino)-2,6-dichloropyrimidine-5-carbaldehyde (1268383-19-2) → tert-butyl [5-(benzyloxy)-4-(di-tert-butylaminodicarbonate)-1,2-dihydro-1-(3,4-dihydroxybutyl)-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate (1268383-27-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0 °C / Inert atmosphere

2.2: Inert atmosphere; Reflux

3.1: dmap; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

4.1: hydroxylamine hydrochloride; potassium hydrogencarbonate / methanol / 0 °C / Inert atmosphere; Reflux

5.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

6.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

7.1: ammonia / methanol / 2 h / 0 °C / Inert atmosphere

8.1: dmap; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

9.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 20 °C

With dmap; osmium(VIII) oxide; hydroxylamine hydrochloride; ammonia; sodium hydride; potassium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1016/j.tetlet.2010.11.122

Reference yield:

4-(benzyloxy)-6-(but-3-enylamino)-2-(methylamino)pyrimidine-5-carbaldehyde (1268383-21-6) → tert-butyl [5-(benzyloxy)-4-(di-tert-butylaminodicarbonate)-1,2-dihydro-1-(3,4-dihydroxybutyl)-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate (1268383-27-2)

Guidance literature:

Multi-step reaction with 7 steps

1: dmap; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

2: hydroxylamine hydrochloride; potassium hydrogencarbonate / methanol / 0 °C / Inert atmosphere; Reflux

3: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

4: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

5: ammonia / methanol / 2 h / 0 °C / Inert atmosphere

6: dmap; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

7: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 20 °C

With dmap; osmium(VIII) oxide; hydroxylamine hydrochloride; ammonia; potassium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1016/j.tetlet.2010.11.122

upstream raw materials:

4-(but-3-enylamino)-2,6-dichloropyrimidine-5-carbaldehyde

4-(but-3-enylamino)-6-chloro-2-(methylamino)pyrimidine-5-carbaldehyde

4-(benzyloxy)-6-(but-3-enylamino)-2-(methylamino)pyrimidine-5-carbaldehyde

tert-butyl [4-(benzyloxy)-6-(but-3-enylamino)-5-formylpyrimidin-2-yl]-N-(methyl)carbamate

Downstream raw materials:

tert-Butyl [5-(benzyloxy)-4-(di-tert butylaminodicarbonate)1,2-dihydro-1-(3-propanal)-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate

tert-butyl [5-(benzylamino)-4-(benzyloxy)-7-oxo-7,8-dihydropyrimido[4,5-d]pyrimidin-2-yl]-N-(methyl)carbamate

C₂₉H₃₈N₆O₈

C₅₀H₅₈N₆O₁₃