N'-[4-[(E)-2-(dimethylamino)ethenyl]-5-nitro-6-oxo-1-(phenylmethoxymethyl)pyrimidin-2-yl]-N,N-dimethylmethanimidamide

Base Information

• Chemical Name: N'-[4-[(E)-2-(dimethylamino)ethenyl]-5-nitro-6-oxo-1-(phenylmethoxymethyl)pyrimidin-2-yl]-N,N-dimethylmethanimidamide
• CAS No.: 518316-53-5
• Molecular Formula: C19H24N6O4
• Molecular Weight: 400.437
• DSSTox Substance ID: DTXSID30447040
• Mol file: 518316-53-5.mol

Synonyms:MET054;DTXSID30447040;518316-53-5

Chemical Property of N'-[4-[(E)-2-(dimethylamino)ethenyl]-5-nitro-6-oxo-1-(phenylmethoxymethyl)pyrimidin-2-yl]-N,N-dimethylmethanimidamide

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 400.18590327
• Heavy Atom Count: 29
• Complexity: 715

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN(C)C=CC1=C(C(=O)N(C(=N1)N=CN(C)C)COCC2=CC=CC=C2)[N+](=O)[O-]
• Isomeric SMILES: CN(C)/C=C/C1=C(C(=O)N(C(=N1)/N=C/N(C)C)COCC2=CC=CC=C2)[N+](=O)[O-]

Technology Process of N'-[4-[(E)-2-(dimethylamino)ethenyl]-5-nitro-6-oxo-1-(phenylmethoxymethyl)pyrimidin-2-yl]-N,N-dimethylmethanimidamide

There total 3 articles about N'-[4-[(E)-2-(dimethylamino)ethenyl]-5-nitro-6-oxo-1-(phenylmethoxymethyl)pyrimidin-2-yl]-N,N-dimethylmethanimidamide 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: 91.0%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + 3-benzyloxymethyl-2-[(dimethylamino)methyleneimino]-6-methyl-5-nitro-4(3H)-oxopyrimidine (518316-52-4) → 3-benzyloxymethyl-2-[(dimethylamino)methyleneimino]-6-[(2-dimethylamino)ethenyl]-5-nitro-4(3H)-oxopyrimidine (518316-53-5)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 40h;

DOI:10.1081/SCC-120015398

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → 3-benzyloxymethyl-2-[(dimethylamino)methyleneimino]-6-[(2-dimethylamino)ethenyl]-5-nitro-4(3H)-oxopyrimidine (518316-53-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 2 h / 20 °C

2: 91 percent / dimethylformamide / 40 h / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide;

DOI:10.1081/SCC-120015398

Reference yield:

2-<<(N,N-Dimethylamino)methylene>amino>-6-methyl-5-nitro-4(3H)-oxopyrimidine (151587-54-1) → 3-benzyloxymethyl-2-[(dimethylamino)methyleneimino]-6-[(2-dimethylamino)ethenyl]-5-nitro-4(3H)-oxopyrimidine (518316-53-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 2 h / 20 °C

2: 91 percent / dimethylformamide / 40 h / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide;

DOI:10.1081/SCC-120015398

upstream raw materials:

N,N-dimethyl-formamide dimethyl acetal

3-benzyloxymethyl-2-[(dimethylamino)methyleneimino]-6-methyl-5-nitro-4(3H)-oxopyrimidine

Benzyloxymethyl chloride

2-<<(N,N-Dimethylamino)methylene>amino>-6-methyl-5-nitro-4(3H)-oxopyrimidine

Downstream raw materials:

1-benzyloxymethyl-9-deazaguanine

9-deazaguanine

3-benzyloxymethyl-2-[(dimethylamino)methyleneimino]-4(3H)-oxo-5H-pyrrolo[3,2-d]pyrimidine