N-(5-Methyl-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

Base Information

• Chemical Name: N-(5-Methyl-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide
• CAS No.: 149712-91-4
• Molecular Formula: C₁₅H₁₉N₃O₂Si
• Molecular Weight: 301.42
• Mol file: 149712-91-4.mol

Synonyms:N-(5-Methyl-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

Chemical Property of N-(5-Methyl-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of N-(5-Methyl-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

There total 1 articles about N-(5-Methyl-2-trimethylsilanyloxy-pyrimidin-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,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + N-(5-methyl-2-oxo-1H-pyrimidin-4-yl)benzamide (126354-30-1) → N-(5-Methyl-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide (149712-91-4)

Guidance literature:

In acetonitrile; for 1h; Inert atmosphere;

DOI:10.1021/acs.oprd.2c00013

Reference yield: 41.0%

<2S(2α,5α)>- and <2S(2α,5β)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-ol acetate (202532-88-5) + N-(5-Methyl-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide (149712-91-4) → (-)-(2S,5S)-5-methyl-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-benzoylcytosine (149819-35-2) + (+)-(2S,5R)-5-methyl-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-benzoylcytosine (149819-34-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; Ambient temperature;

DOI:10.1021/jm00070a006

Reference yield:

N-(5-Methyl-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide (149712-91-4) → N-[1-((2S,5S)-2-Hydroxymethyl-[1,3]oxathiolan-5-yl)-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

Guidance literature:

Multi-step reaction with 2 steps

1: 27 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / Ambient temperature

2: tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1021/jm00070a006

upstream raw materials:

N,O-bis-(trimethylsilyl)-acetamide

N-(5-methyl-2-oxo-1H-pyrimidin-4-yl)benzamide

Downstream raw materials:

(-)-(2S,5S)-5-methyl-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-benzoylcytosine

(+)-(2S,5R)-5-methyl-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-benzoylcytosine

N-[5-Methyl-2-oxo-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-methoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1,2-dihydro-pyrimidin-4-yl]-benzamide

N⁴-benzoyl-2'-O-methyl-5-methylcytidine