4-amino-5-[1-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-imidazol-4-yl]-1H-pyrimidin-2-one

Base Information

• Chemical Name: 4-amino-5-[1-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-imidazol-4-yl]-1H-pyrimidin-2-one
• CAS No.: 1054665-79-0
• Molecular Formula: C₃₃H₃₃N₅O₅
• Molecular Weight: 579.656

Synonyms:4-amino-5-[1-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-imidazol-4-yl]-1H-pyrimidin-2-one

Chemical Property of 4-amino-5-[1-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-imidazol-4-yl]-1H-pyrimidin-2-one

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Technology Process of 4-amino-5-[1-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-imidazol-4-yl]-1H-pyrimidin-2-one

There total 6 articles about 4-amino-5-[1-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-imidazol-4-yl]-1H-pyrimidin-2-one 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:

5-[1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-imidazol-4-yl]-pyrimidine-2,4-diamine (848945-15-3) → 4-amino-5-[1-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-imidazol-4-yl]-1H-pyrimidin-2-one (1054665-79-0)

Guidance literature:

With acetic acid; sodium nitrite; In tetrahydrofuran; water; at 60 ℃; for 2h;

DOI:10.1021/jo048218h

Reference yield:

1-(4,5-diiodoimidazol-3-yl)-β-D-ribofuranose (848945-11-9) → 4-amino-5-[1-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-imidazol-4-yl]-1H-pyrimidin-2-one (1054665-79-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 18 h / 20 °C

2: 80 percent / EtMgBr / diethyl ether / 3 h / 20 °C

3: 70 percent / NaHCO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 4 h / Heating

4: 52 percent / NH₃ / methanol / 96 h / 170 °C

5: sodium nitrite; glacial acetic acid / tetrahydrofuran; H₂O / 2 h / 60 °C

With ethylmagnesium bromide; ammonia; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; acetic acid; sodium nitrite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; water; 3: Suzuki coupling;

DOI:10.1021/jo048218h

Reference yield:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4,5-diiodo-imidazol-1-yl)-tetrahydro-furan-3-yl ester (848945-10-8) → 4-amino-5-[1-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-imidazol-4-yl]-1H-pyrimidin-2-one (1054665-79-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 52.8 g / ammonium hydroxide / ethanol / 18 h / 20 °C

2: 80 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 18 h / 20 °C

3: 80 percent / EtMgBr / diethyl ether / 3 h / 20 °C

4: 70 percent / NaHCO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 4 h / Heating

5: 52 percent / NH₃ / methanol / 96 h / 170 °C

6: sodium nitrite; glacial acetic acid / tetrahydrofuran; H₂O / 2 h / 60 °C

With ammonium hydroxide; ethylmagnesium bromide; ammonia; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; acetic acid; sodium nitrite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; water; 4: Suzuki coupling;

DOI:10.1021/jo048218h

upstream raw materials:

5-[1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-imidazol-4-yl]-pyrimidine-2,4-diamine

1-(4,5-diiodoimidazol-3-yl)-β-D-ribofuranose

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4,5-diiodo-imidazol-1-yl)-tetrahydro-furan-3-yl ester

1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4-iodo-1H-imidazole

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