(S)-8-ethyl-8-hydroxy-4-methoxy-7-oxo-N-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2-carboxamide

Base Information

• Chemical Name: (S)-8-ethyl-8-hydroxy-4-methoxy-7-oxo-N-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2-carboxamide
• CAS No.: 1236303-41-5
• Molecular Formula: C₁₇H₁₇N₃O₅
• Molecular Weight: 343.339
• Mol file: 1236303-41-5.mol

Synonyms:(S)-8-ethyl-8-hydroxy-4-methoxy-7-oxo-N-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2-carboxamide

Chemical Property of (S)-8-ethyl-8-hydroxy-4-methoxy-7-oxo-N-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-8-ethyl-8-hydroxy-4-methoxy-7-oxo-N-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2-carboxamide

There total 6 articles about (S)-8-ethyl-8-hydroxy-4-methoxy-7-oxo-N-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2-carboxamide 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:

C17H19N3O5 → (S)-8-ethyl-8-hydroxy-4-methoxy-7-oxo-N-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2-carboxamide (1236303-41-5)

Guidance literature:

With iodine; calcium carbonate; In methanol; water; at 40 ℃; for 15h; Inert atmosphere;

DOI:10.1002/asia.201000073

Reference yield:

8-ethyl-4-methoxy-N-phenyl-5H-pyrano[4,3-d]pyrimidine-2-carboxamide (1236303-37-9) → (S)-8-ethyl-8-hydroxy-4-methoxy-7-oxo-N-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2-carboxamide (1236303-41-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium osmate(VI) dihydrate; methanesulfonamide; potassium carbonate; hydroquinidine (2,5-diphenyl-4,6-pyrimidinediyl) diether; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 0 - 20 °C / Inert atmosphere

2: iodine; calcium carbonate / methanol; water / 15 h / 40 °C / Inert atmosphere

With potassium osmate(VI) dihydrate; methanesulfonamide; iodine; potassium carbonate; hydroquinidine (2,5-diphenyl-4,6-pyrimidinediyl) diether; calcium carbonate; potassium hexacyanoferrate(III); In methanol; water; tert-butyl alcohol; 1: Sharpless dihydroxylation;

DOI:10.1002/asia.201000073

Reference yield:

2-chloro-8-ethyl-4-methoxy-5H-pyrano[4,3-d]pyrimidine (848891-83-8) → (S)-8-ethyl-8-hydroxy-4-methoxy-7-oxo-N-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2-carboxamide (1236303-41-5)

Guidance literature:

Multi-step reaction with 6 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine / 5 h / 90 °C / 6965.99 Torr / Inert atmosphere

2: lithium hydroxide monohydrate; water / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 °C / Inert atmosphere

4: sodium hydrogencarbonate / dichloromethane / 2 h / Inert atmosphere

5: potassium osmate(VI) dihydrate; methanesulfonamide; potassium carbonate; hydroquinidine (2,5-diphenyl-4,6-pyrimidinediyl) diether; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 0 - 20 °C / Inert atmosphere

6: iodine; calcium carbonate / methanol; water / 15 h / 40 °C / Inert atmosphere

With potassium osmate(VI) dihydrate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; oxalyl dichloride; lithium hydroxide monohydrate; methanesulfonamide; water; iodine; sodium hydrogencarbonate; potassium carbonate; triethylamine; N,N-dimethyl-formamide; hydroquinidine (2,5-diphenyl-4,6-pyrimidinediyl) diether; calcium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; 5: Sharpless dihydroxylation;

DOI:10.1002/asia.201000073

upstream raw materials:

2-chloro-8-ethyl-4-methoxy-5H-pyrano[4,3-d]pyrimidine

8-ethyl-4-methoxy-5H-pyrano[4,3-d]pyrimidine-2-carboxylic acid

methyl 8-ethyl-4-methoxy-5H-pyrano[4,3-d]pyrimidine-2-carboxylate

8-ethyl-4-methoxy-N-phenyl-5H-pyrano[4,3-d]pyrimidine-2-carboxamide

Downstream raw materials:

(S)-8-ethyl-4,7-dioxo-2-(phenylcarbamoyl)-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-8-yl acetate

C₂₁H₁₉N₃O₆

(S)-8-ethyl-8-hydroxy-4,7-dioxo-N-phenyl-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidine-2-carboxamide

(S)-3-allyl-8-ethyl-4,7-dioxo-2-(phenylcarbamoyl)-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-8-yl acetate