2-[(DiMethylaMino)Methylene]aMino-3N-(pivaloyloxy)Methyl-6-Methyl-5-nitro-4-pyriMidinol

Base Information

• Chemical Name: 2-[(DiMethylaMino)Methylene]aMino-3N-(pivaloyloxy)Methyl-6-Methyl-5-nitro-4-pyriMidinol
• CAS No.: 151587-55-2
• Molecular Formula: C₁₄H₂₁N₅O₅
• Molecular Weight: 339.351
• Mol file: 151587-55-2.mol

Synonyms:2-[(DiMethylaMino)Methylene]aMino-3N-(pivaloyloxy)Methyl-6-Methyl-5-nitro-4-pyriMidinol;2,2-DiMethyl-propanoic Acid [2-[[(DiMethylaMino)Methylene]aMino]-4-Methyl-5-nitro-6-oxo-1(6H)-pyriMidinyl]Methyl Ester

Chemical Property of 2-[(DiMethylaMino)Methylene]aMino-3N-(pivaloyloxy)Methyl-6-Methyl-5-nitro-4-pyriMidinol

Chemical Property:

• PSA: 122.61000
• LogP: 1.75130
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

98% ^*data from raw suppliers

2-[(Dimethylamino)methylene]amino-3N-(pivaloyloxy)methyl-6-methyl-5-nitro-4-pyrimidinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(DiMethylaMino)Methylene]aMino-3N-(pivaloyloxy)Methyl-6-Methyl-5-nitro-4-pyriMidinol

There total 4 articles about 2-[(DiMethylaMino)Methylene]aMino-3N-(pivaloyloxy)Methyl-6-Methyl-5-nitro-4-pyriMidinol 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: 60.0%

Chloromethyl pivalate (18997-19-8) + 2-<<(N,N-Dimethylamino)methylene>amino>-6-methyl-5-nitro-4(3H)-oxopyrimidine (151587-54-1) → 2-<<(N,N-Dimethylamino)methylene>amino>-6-methyl-5-nitro-4-<(pivaloyloxy)methoxy>pyrimidine + 2-<<(N,N-Dimethylamino)methylene>amino>-6-methyl-5-nitro-4(3H)-oxo-3-<(pivaloyloxy)methyl>pyrimidine (151587-55-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; 1.) r.t., 1 h, 2.) r.t., 12 h;

DOI:10.1021/jo00129a040

Reference yield:

2-amino-6-methyl-5-nitro-4(3H)-oxopyrimidine (4214-85-1) → 2-<<(N,N-Dimethylamino)methylene>amino>-6-methyl-5-nitro-4(3H)-oxo-3-<(pivaloyloxy)methyl>pyrimidine (151587-55-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1021/jo00129a040

Reference yield:

2-amino-6-methyl-3H-pyrimidin-4-one (3977-29-5) → 2-<<(N,N-Dimethylamino)methylene>amino>-6-methyl-5-nitro-4(3H)-oxo-3-<(pivaloyloxy)methyl>pyrimidine (151587-55-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / conc. HNO₃, conc. H₂SO₄ / 3 h / Ambient temperature

2: 91 percent / CH₂Cl₂ / 5 h / Ambient temperature

3: 60 percent / NaH / dimethylformamide / 1.) r.t., 1 h, 2.) r.t., 12 h

With sulfuric acid; nitric acid; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00129a040

upstream raw materials:

Chloromethyl pivalate

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

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

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

Downstream raw materials:

Dimethyl N-<4-<2-<2-<<(N,N-dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidin-5-yl>ethyl>benzoyl>-L-glutamate

Dimethyl N-<4-<3-<2-<<(N,N-dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidin-5-yl>propyl>benzoyl>-L-glutamate

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

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

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.