2,4(1H,3H)-dioxo-6-(4-methoxymethoxyphenyl)-1-(2-methylthiobenzyl)-5-(methanesulfonamidomethyl)-thieno[2,3-d]pyrimidine-3-acetic acid

Base Information

• Chemical Name: 2,4(1H,3H)-dioxo-6-(4-methoxymethoxyphenyl)-1-(2-methylthiobenzyl)-5-(methanesulfonamidomethyl)-thieno[2,3-d]pyrimidine-3-acetic acid
• CAS No.: 188478-81-1
• Molecular Formula: C₂₆H₂₇N₃O₈S₃
• Molecular Weight: 605.714

Synonyms:2,4(1H,3H)-dioxo-6-(4-methoxymethoxyphenyl)-1-(2-methylthiobenzyl)-5-(methanesulfonamidomethyl)-thieno[2,3-d]pyrimidine-3-acetic acid

Chemical Property of 2,4(1H,3H)-dioxo-6-(4-methoxymethoxyphenyl)-1-(2-methylthiobenzyl)-5-(methanesulfonamidomethyl)-thieno[2,3-d]pyrimidine-3-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 2,4(1H,3H)-dioxo-6-(4-methoxymethoxyphenyl)-1-(2-methylthiobenzyl)-5-(methanesulfonamidomethyl)-thieno[2,3-d]pyrimidine-3-acetic acid

There total 14 articles about 2,4(1H,3H)-dioxo-6-(4-methoxymethoxyphenyl)-1-(2-methylthiobenzyl)-5-(methanesulfonamidomethyl)-thieno[2,3-d]pyrimidine-3-acetic acid 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: 71.0%

ethyl 6-(4-methoxymethoxyphenyl)-5-(methylsulfonylaminomethyl)-1-(2-methylthiobenzyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno<2,3-d>pyrimidine-3-acetate (188478-67-3) → 2,4(1H,3H)-dioxo-6-(4-methoxymethoxyphenyl)-1-(2-methylthiobenzyl)-5-(methanesulfonamidomethyl)-thieno[2,3-d]pyrimidine-3-acetic acid (188478-81-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; for 1.5h; Ambient temperature;

DOI:10.1248/cpb.46.1724

Reference yield:

4-methoxybenzyl methyl ketone (122-84-9) → 2,4(1H,3H)-dioxo-6-(4-methoxymethoxyphenyl)-1-(2-methylthiobenzyl)-5-(methanesulfonamidomethyl)-thieno[2,3-d]pyrimidine-3-acetic acid (188478-81-1)

Guidance literature:

Multi-step reaction with 13 steps

1: NH₄OAc, AcOH / benzene / 24 h / Heating

2: S, Et₂NH / ethanol / 2 h / 60 °C

3: 1.) pyridine, 2.) NaOEt / 1.) 45 deg C, 3 h, 2.) EtOH, RT, 1.5 h

4: 85 percent / AlCl₃, dimethyl disulfide / CH₂Cl₂ / 20 h / Ambient temperature

5: pyridine / 3 h / Ambient temperature

6: K₂CO₃ / dimethylformamide / 13 h / Ambient temperature

7: 78 percent / aq. K₂CO₃ / methanol; tetrahydrofuran / 0.67 h / Ambient temperature

8: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 3 h

9: 82 percent / NBS, 2,2'-azobis(isobutyronitrile) / CCl₄ / 2 h / Heating

10: 75 percent / dimethylformamide / 4 h / Ambient temperature

11: 84 percent / hydrazine monohydrate / ethanol / 16 h / 80 °C

12: 100 percent / Et₃N / CH₂Cl₂ / 30 h / 0 °C

13: 71 percent / 1N aq. NaOH / methanol; tetrahydrofuran / 1.5 h / Ambient temperature

With pyridine; sodium hydroxide; N-Bromosuccinimide; aluminium trichloride; 2,2'-azobis(isobutyronitrile); Dimethyldisulphide; ammonium acetate; sodium ethanolate; sodium hydride; potassium carbonate; hydrazine hydrate; acetic acid; diethylamine; triethylamine; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.46.1724

Reference yield:

1-chloromethyl-2-methylsulfanylbenzene (26190-68-1) → 2,4(1H,3H)-dioxo-6-(4-methoxymethoxyphenyl)-1-(2-methylthiobenzyl)-5-(methanesulfonamidomethyl)-thieno[2,3-d]pyrimidine-3-acetic acid (188478-81-1)

Guidance literature:

Multi-step reaction with 8 steps

1: K₂CO₃ / dimethylformamide / 13 h / Ambient temperature

2: 78 percent / aq. K₂CO₃ / methanol; tetrahydrofuran / 0.67 h / Ambient temperature

3: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 3 h

4: 82 percent / NBS, 2,2'-azobis(isobutyronitrile) / CCl₄ / 2 h / Heating

5: 75 percent / dimethylformamide / 4 h / Ambient temperature

6: 84 percent / hydrazine monohydrate / ethanol / 16 h / 80 °C

7: 100 percent / Et₃N / CH₂Cl₂ / 30 h / 0 °C

8: 71 percent / 1N aq. NaOH / methanol; tetrahydrofuran / 1.5 h / Ambient temperature

With sodium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sodium hydride; potassium carbonate; hydrazine hydrate; triethylamine; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.46.1724

upstream raw materials:

ethyl 6-(4-methoxymethoxyphenyl)-5-(methylsulfonylaminomethyl)-1-(2-methylthiobenzyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno<2,3-d>pyrimidine-3-acetate

4-methoxybenzyl methyl ketone

1-chloromethyl-2-methylsulfanylbenzene

2-amino-4-methyl-5-(4-methoxyphenyl)thiophene-3-carboxylic acid ethyl ester

Downstream raw materials:

pivaloyloxymethyl 2,4(1H,3H)-dioxo-6-(4-methoxymethoxyphenyl)-1-(2-methylthiobenzyl)-5-(methanesulfonamidomethyl)-thieno[2,3-d]pyrimidine-3-acetate

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