4-{5-[2-(2,4-diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-ethyl]-pyridin-3-yl}-benzoic acid methyl ester

Base Information

Chemical Name:4-{5-[2-(2,4-diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-ethyl]-pyridin-3-yl}-benzoic acid methyl ester
CAS No.:289677-55-0
Molecular Formula:C₁₉H₁₉N₅O₃
Molecular Weight:365.392
Hs Code.:

Synonyms:4-{5-[2-(2,4-diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-ethyl]-pyridin-3-yl}-benzoic acid methyl ester

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Chemical Property of 4-{5-[2-(2,4-diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-ethyl]-pyridin-3-yl}-benzoic acid methyl ester

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Technology Process of 4-{5-[2-(2,4-diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-ethyl]-pyridin-3-yl}-benzoic acid methyl ester

There total 6 articles about 4-{5-[2-(2,4-diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-ethyl]-pyridin-3-yl}-benzoic acid methyl ester 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: 56.0%

: 50-01-1
guanidine hydrochloride

: 289677-54-9
methyl 4-[5-[3-carboethoxy-3-cyanobut-1-yl]-3-pyridinyl]benzoate

: 289677-55-0
4-{5-[2-(2,4-diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-ethyl]-pyridin-3-yl}-benzoic acid methyl ester

Guidance literature:: With sodium ethanolate; In ethanol; at 45 ℃; for 12h;
DOI:10.1016/S0968-0896(00)00051-1

Reference yield:

: 619-42-1
4-methoxycarbonylphenyl bromide

: 289677-55-0
4-{5-[2-(2,4-diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-ethyl]-pyridin-3-yl}-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: diboron pinacol ester; KOAc; PdCl₂(dppf) / dimethylformamide / 2 h / 80 °C

1.2: 63 percent / PdCl₂(dppf); aq. Na₂CO₃ / dimethylformamide / 12 h / 80 °C

2.1: 91 percent / Bu₄NF / tetrahydrofuran / 3 h / 25 °C

3.1: 87 percent / SOCl₂ / CH₂Cl₂ / 3 h / 50 °C

4.1: 63 percent / K₂CO₃ / dimethylformamide / 3 h / 70 °C

5.1: 56 percent / NaOEt / ethanol / 12 h / 45 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; thionyl chloride; tetrabutyl ammonium fluoride; sodium ethanolate; potassium acetate; potassium carbonate; bis(pinacol)diborane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Substitution / 1.2: Condensation / 2.1: silyl ether cleavage / 3.1: Chlorination / 4.1: Alkylation / 5.1: cyclocondensation;
DOI:10.1016/S0968-0896(00)00051-1

Reference yield:

: 3-bromo-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-pyridine

: 289677-55-0
4-{5-[2-(2,4-diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-ethyl]-pyridin-3-yl}-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: diboron pinacol ester; KOAc; PdCl₂(dppf) / dimethylformamide / 2 h / 80 °C

1.2: 63 percent / PdCl₂(dppf); aq. Na₂CO₃ / dimethylformamide / 12 h / 80 °C

2.1: 91 percent / Bu₄NF / tetrahydrofuran / 3 h / 25 °C

3.1: 87 percent / SOCl₂ / CH₂Cl₂ / 3 h / 50 °C

4.1: 63 percent / K₂CO₃ / dimethylformamide / 3 h / 70 °C

5.1: 56 percent / NaOEt / ethanol / 12 h / 45 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; thionyl chloride; tetrabutyl ammonium fluoride; sodium ethanolate; potassium acetate; potassium carbonate; bis(pinacol)diborane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Substitution / 1.2: Condensation / 2.1: silyl ether cleavage / 3.1: Chlorination / 4.1: Alkylation / 5.1: cyclocondensation;
DOI:10.1016/S0968-0896(00)00051-1