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

Base Information

• Chemical Name: 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
• CAS No.: 1268383-06-7
• Molecular Formula: C₃₂H₄₂N₆O₉
• Molecular Weight: 654.72

Synonyms: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

Chemical Property of 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

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-propanal)-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate

There total 11 articles about 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 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: 89.0%

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) → 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 (1268383-06-7)

Guidance literature:

With sodium periodate; In dichloromethane; water; at 20 ℃;

DOI:10.1016/j.tetlet.2010.11.122

Reference yield:

4-(but-3-enylamino)-6-chloro-2-(methylamino)pyrimidine-5-carbaldehyde (1268383-20-5) → 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 (1268383-06-7)

Guidance literature:

Multi-step reaction with 9 steps

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

1.2: Inert atmosphere; Reflux

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

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

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

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

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

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

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

9.1: sodium periodate / dichloromethane; water / 20 °C

With dmap; sodium periodate; 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-(but-3-enylamino)-2,6-dichloropyrimidine-5-carbaldehyde (1268383-19-2) → 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 (1268383-06-7)

Guidance literature:

Multi-step reaction with 10 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

10.1: sodium periodate / dichloromethane; water / 20 °C

With dmap; sodium periodate; 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

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:

C₅₀H₅₈N₆O₁₃

(2R,3S,5R)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

(2R,3S,5S)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

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

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