[2-[(E)-dimethylaminomethylideneamino]-4-oxo-5H-pyrrolo[3,2-d]pyrimidin-3-yl]methyl 2,2-dimethylpropanoate

Base Information

• Chemical Name: [2-[(E)-dimethylaminomethylideneamino]-4-oxo-5H-pyrrolo[3,2-d]pyrimidin-3-yl]methyl 2,2-dimethylpropanoate
• CAS No.: 151587-58-5
• Molecular Formula: C15H21N5O3
• Molecular Weight: 319.35900
• DSSTox Substance ID: DTXSID50471923
• Mol file: 151587-58-5.mol

Synonyms:151587-58-5;N1-(Pivaloyloxy)methyl-N2-(dimethylamino)methylene 9-Deazaguanine;[2-[(E)-dimethylaminomethylideneamino]-4-oxo-5H-pyrrolo[3,2-d]pyrimidin-3-yl]methyl 2,2-dimethylpropanoate;(2-(((Dimethylamino)methylene)amino)-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-3-yl)methyl pivalate;FT-0673957;DTXSID50471923;A937690

Chemical Property of [2-[(E)-dimethylaminomethylideneamino]-4-oxo-5H-pyrrolo[3,2-d]pyrimidin-3-yl]methyl 2,2-dimethylpropanoate

Chemical Property:

• PSA: 92.58000
• LogP: 1.49280
• Solubility.: Dichloromethane, Ethyl Acetate
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 319.16443955
• Heavy Atom Count: 23
• Complexity: 536

Purity/Quality:

97% ^*data from raw suppliers

N1-(Pivaloyloxy)methyl-N2-(dimethylamino)methylene9-Deazaguanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)OCN1C(=O)C2=C(C=CN2)N=C1N=CN(C)C
• Isomeric SMILES: CC(C)(C)C(=O)OCN1C(=O)C2=C(C=CN2)N=C1/N=C/N(C)C
• Uses: 9-Deazaguanosine intermendiate.

Technology Process of [2-[(E)-dimethylaminomethylideneamino]-4-oxo-5H-pyrrolo[3,2-d]pyrimidin-3-yl]methyl 2,2-dimethylpropanoate

There total 7 articles about [2-[(E)-dimethylaminomethylideneamino]-4-oxo-5H-pyrrolo[3,2-d]pyrimidin-3-yl]methyl 2,2-dimethylpropanoate 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: 94.0%

4-<(2(E)-Dimethylamino)ethenyl>-2-<<(N,N-dimethylamino)methylene>amino>-5-nitro-4(3H)-oxo-3-<(pivaloyloxy)methyl>pyrimidine → 2-<<(N,N-Dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidine (151587-58-5)

Guidance literature:

With sodium dithionite; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1021/jo00129a040

Reference yield: 94.0%

2,2-Dimethyl-propionic acid 2-(dimethylamino-methyleneamino)-4-((E)-2-dimethylamino-vinyl)-5-nitro-6-oxo-6H-pyrimidin-1-ylmethyl ester (151587-57-4) → 2-<<(N,N-Dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidine (151587-58-5)

Guidance literature:

With sodium dithionite;

DOI:10.1016/S0040-4039(00)60633-0

Reference yield:

2-amino-6-methyl-5-nitro-4(3H)-oxopyrimidine (4214-85-1) → 2-<<(N,N-Dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidine (151587-58-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / CH₂Cl₂ / 5 h / Ambient temperature

2: 60 percent / NaH / dimethylformamide / 1.) r.t., 1 h, 2.) r.t., 12 h

3: 86 percent / dimethylformamide / 12 h / Ambient temperature

4: 94 percent / aq. Na₂S₂O₄ / tetrahydrofuran / 1 h / Ambient temperature

With sodium dithionite; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00129a040

upstream raw materials:

2,2-Dimethyl-propionic acid 2-(dimethylamino-methyleneamino)-4-((E)-2-dimethylamino-vinyl)-5-nitro-6-oxo-6H-pyrimidin-1-ylmethyl ester

2-amino-6-methyl-5-nitro-4(3H)-oxopyrimidine

2-amino-6-methyl-3H-pyrimidin-4-one

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

Downstream raw materials:

tert-Butyl 4-<3-<2-<<(N,N-dimethylamino)methylene>amino>-3-<(pivaloyloxy)methyl>-4(3H)-oxo-5H-pyrrolo<3,2-d>pyrimidin-5-yl>propyl>benzoate

4-t-butyloxycarbonylstyrene

tert-Butyl 4-<2-<2-<<(N,N-dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidin-5-yl>ethyl>benzoate

4-<2-<2-<<(N,N-Dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidin-5-yl>ethyl>benzoic acid

Refernces

• 1、 Taylor, Edward C.,Young, Wendy B.. "Pyrrolopyrimidine Folate Analogues: "Inverted" Analogues of the Cytotoxic Agent LY231514". . p. 7947 - 7952. Retrieved 2007/10/03.