6-Benzyl-1-benzyloxymethyl-5-isopropyl uracil

Base Information

• Chemical Name: 6-Benzyl-1-benzyloxymethyl-5-isopropyl uracil
• CAS No.: 175739-42-1
• Molecular Formula: C22H24N2O3
• Molecular Weight: 364.437560
• UNII: 2HRU1H9M1I
• DSSTox Substance ID: DTXSID60170016
• Nikkaji Number: J713.893H
• Wikidata: Q27097826
• Metabolomics Workbench ID: 56639
• ChEMBL ID: CHEMBL436546
• Mol file: 175739-42-1.mol

Synonyms:TNK-651

Chemical Property of 6-Benzyl-1-benzyloxymethyl-5-isopropyl uracil

Chemical Property:

• Refractive Index: 1.582
• Density: 1.172 g/cm³
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 364.17869263
• Heavy Atom Count: 27
• Complexity: 558

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(N(C(=O)NC1=O)COCC2=CC=CC=C2)CC3=CC=CC=C3

Technology Process of 6-Benzyl-1-benzyloxymethyl-5-isopropyl uracil

There total 8 articles about 6-Benzyl-1-benzyloxymethyl-5-isopropyl uracil 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: 86.5%

Benzyloxymethyl chloride (3587-60-8) + 6-benzyl-5-isopropylpyrimidine-2,4(1H,3H)-dione (176519-55-4) → 6-benzyl-1-[(benzyloxy)methyl]-5-isopropylpyrimidine-2,4(1H,3H)-dione (175739-42-1)

Guidance literature:

6-benzyl-5-isopropylpyrimidine-2,4(1H,3H)-dione; With N,O-bis-(trimethylsilyl)-acetamide; In dichloromethane;

Benzyloxymethyl chloride; With lithium iodide; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1002/jhet.987

Reference yield:

ethyl 2-isopropyl-3-oxo-4-phenylbutanoate (176519-53-2) → 6-benzyl-1-[(benzyloxy)methyl]-5-isopropylpyrimidine-2,4(1H,3H)-dione (175739-42-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butylate / isopropyl alcohol / Inert atmosphere

1.2: Inert atmosphere

2.1: N,O-bis-(trimethylsilyl)-acetamide; tetra-(n-butyl)ammonium iodide / dichloromethane / 20 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; In dichloromethane; isopropyl alcohol;

DOI:10.1021/ml1002162

Reference yield:

ethyl 2-bromoisovalerate (609-12-1) → 6-benzyl-1-[(benzyloxy)methyl]-5-isopropylpyrimidine-2,4(1H,3H)-dione (175739-42-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: iodine; zinc / tetrahydrofuran / Inert atmosphere

2.1: potassium tert-butylate / isopropyl alcohol / Inert atmosphere

2.2: Inert atmosphere

3.1: N,O-bis-(trimethylsilyl)-acetamide; tetra-(n-butyl)ammonium iodide / dichloromethane / 20 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; potassium tert-butylate; iodine; tetra-(n-butyl)ammonium iodide; zinc; In tetrahydrofuran; dichloromethane; isopropyl alcohol;

DOI:10.1021/ml1002162

upstream raw materials:

ethyl 2-bromoisovalerate

Benzyloxymethyl chloride

6-benzyl-5-isopropylpyrimidine-2,4(1H,3H)-dione

ethyl 2-isopropyl-3-oxo-4-phenylbutanoate

Refernces

• 1、 Tang, Jing,Maddali, Kasthuraiah,Dreis, Christine D.,Sham, Yuk Y.,Vince, Robert,Pommier, Yves,Wang, Zhengqiang. "N-3 hydroxylation of pyrimidine-2,4-diones yields dual inhibitors of HIV reverse transcriptase and integrase". . p. 63 - 67. Retrieved 2011/04/17.