Benzoic acid, 4-(1,3-diamino-7,8,9,10-tetrahydropyrimido[4,5-c]isoquinolin-8-yl)-, methyl ester

Base Information

Chemical Name:Benzoic acid, 4-(1,3-diamino-7,8,9,10-tetrahydropyrimido[4,5-c]isoquinolin-8-yl)-, methyl ester
CAS No.:137465-04-4
Molecular Formula:C19H19N5O2
Molecular Weight:349.392
Hs Code.:

Synonyms:

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Chemical Property of Benzoic acid, 4-(1,3-diamino-7,8,9,10-tetrahydropyrimido[4,5-c]isoquinolin-8-yl)-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:: SDS file from LookChem

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Technology Process of Benzoic acid, 4-(1,3-diamino-7,8,9,10-tetrahydropyrimido[4,5-c]isoquinolin-8-yl)-, methyl ester

There total 12 articles about Benzoic acid, 4-(1,3-diamino-7,8,9,10-tetrahydropyrimido[4,5-c]isoquinolin-8-yl)-, 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: 61.0%

: 137465-03-3
4-(1,3-Diamino-5,6,7,8,9,10-hexahydro-pyrimido[4,5-c]isoquinolin-8-yl)-benzoic acid methyl ester

: 137465-04-4
methyl 4-amino-4-deoxy-5,10-ethano-5,10-dideazapteroate

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetic acid; for 18h; Ambient temperature;
DOI:10.1021/jm00080a017

Reference yield:

: 4746-97-8
cyclohexanedione monoethylene ketal

: 137465-04-4
methyl 4-amino-4-deoxy-5,10-ethano-5,10-dideazapteroate

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) n-BuLi / 1.) THF, hexane, -100 deg C to -95 deg C, 10 min, 2.) THF, hexane, -100 deg C to -95 deg C, 10 min

2: 94 percent / aq. NaOH / 2-methoxy-ethanol / 15 h / Heating

3: HCl conc. / 4 h / Heating

4: 39 percent / H₂, HCl conc. / Pd / dioxane / 20 h / 40 - 48 °C

5: 1.) NaH, 2.) KH / 1.) THF, reflux, 2.) THF, reflux, 2 h

6: 82 percent / diphenyl ether / 4 h / 190 - 205 °C

7: 56 percent / BH₃*THF / tetrahydrofuran / 16 h / Ambient temperature

8: 61 percent / DDQ / acetic acid / 18 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; n-butyllithium; borane-THF; hydrogen; potassium hydride; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium; In tetrahydrofuran; 1,4-dioxane; diphenylether; 2-methoxy-ethanol; acetic acid;
DOI:10.1021/jm00080a017

Reference yield:

: 623-00-7
4-bromobenzenecarbonitrile

: 137465-04-4
methyl 4-amino-4-deoxy-5,10-ethano-5,10-dideazapteroate

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) n-BuLi / 1.) THF, hexane, -100 deg C to -95 deg C, 10 min, 2.) THF, hexane, -100 deg C to -95 deg C, 10 min

2: 94 percent / aq. NaOH / 2-methoxy-ethanol / 15 h / Heating

3: HCl conc. / 4 h / Heating

4: 39 percent / H₂, HCl conc. / Pd / dioxane / 20 h / 40 - 48 °C

5: 1.) NaH, 2.) KH / 1.) THF, reflux, 2.) THF, reflux, 2 h

6: 82 percent / diphenyl ether / 4 h / 190 - 205 °C

7: 56 percent / BH₃*THF / tetrahydrofuran / 16 h / Ambient temperature

8: 61 percent / DDQ / acetic acid / 18 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; n-butyllithium; borane-THF; hydrogen; potassium hydride; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium; In tetrahydrofuran; 1,4-dioxane; diphenylether; 2-methoxy-ethanol; acetic acid;
DOI:10.1021/jm00080a017