(R)-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

Base Information

• Chemical Name: (R)-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide
• CAS No.: 148873-45-4
• Molecular Formula: C₁₄H₁₅N₃O₄
• Molecular Weight: 289.291

Synonyms:(R)-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

Chemical Property of (R)-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

Chemical Property:

Purity/Quality:

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Technology Process of (R)-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

There total 4 articles about (R)-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 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:

N-(1-allyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (648881-65-6) → (S)-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (62853-19-4) + (R)-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (148873-45-4)

Guidance literature:

With potassium osmate; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 0 - 20 ℃; Overall yield = 96 %;

DOI:10.1021/acs.joc.8b02442

Reference yield:

Butyric acid (R)-3-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxy-propyl ester → (R)-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (148873-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.05 M CH₃ONa / methanol / 16 h

2: 1.) pyridine, chlorotrimethylsilane, 3.) conc. NH₃

With pyridine; ammonium hydroxide; chloro-trimethyl-silane; sodium methylate; In methanol;

DOI:10.1135/cccc19930649

Reference yield:

4-N-benzoylcytosine (26661-13-2) → (S)-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (62853-19-4) + (R)-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (148873-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 45 h / 60 °C

1.2: 10 h / 60 °C

2.1: potassium carbonate; potassium osmate; potassium hexacyanoferrate(III); methanesulfonamide; hydroquinidein 1,4-phthalazinediyl diether / water; tert-butyl alcohol / 0 - 20 °C

With potassium osmate; methanesulfonamide; sodium hydride; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); In tetrahydrofuran; water; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol;

DOI:10.1021/acs.joc.8b02442

upstream raw materials:

benzoyl chloride

1-(R)-(2,3-dihydroxypropyl)cytosine

N-(1-allyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

4-N-benzoylcytosine

Downstream raw materials:

N⁴-benzoyl-9-(R)-(2-hydroxy-3-triphenylmethoxypropyl)cytosine

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