4-<3-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-1-methylpropyl>benzoic acid

Base Information

• Chemical Name: 4-<3-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-1-methylpropyl>benzoic acid
• CAS No.: 149325-61-1
• Molecular Formula: C₁₈H₂₂N₄O₂
• Molecular Weight: 326.398
• Mol file: 149325-61-1.mol

Synonyms:4-<3-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-1-methylpropyl>benzoic acid

Chemical Property of 4-<3-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-1-methylpropyl>benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-<3-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-1-methylpropyl>benzoic acid

There total 10 articles about 4-<3-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-1-methylpropyl>benzoic 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: 100.0%

tert-butyl 4-<3-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-1-methylpropyl>benzoate (170799-58-3) → 4-<3-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-1-methylpropyl>benzoic acid (149325-61-1)

Guidance literature:

With hydrogenchloride; In acetic acid; for 2h; Ambient temperature;

DOI:10.1248/cpb.43.829

Reference yield:

4-acetylbenzoic acid tert-butyl ester (105580-41-4) → 4-<3-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-1-methylpropyl>benzoic acid (149325-61-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, 60 deg C, 3 h

2: 100 percent / H₂ / 10percent Pd/C / ethanol

3: 98 percent / 1N NaOH / ethanol / 3 h / Ambient temperature

4: 100 percent / NaBH₄, BF₃*Et₂O / tetrahydrofuran / -78 - 20 °C

5: 22 g / triethylamine / CH₂Cl₂ / 1 h / -78 °C

6: 94 percent / NaI / acetone / 12 h / Heating

7: 18.8 percent / tributyltin hydride, azobisisobutyronitrile / benzene / Heating

8: 96 percent / N,N-diisopropylethylamine / hexane; ethanol; acetonitrile / 5 h / Ambient temperature

9: 51 percent / 2-methyl-propan-2-ol / 12 h / 160 °C

10: 100 percent / 1N HCl / acetic acid / 2 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetic acid; acetone; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.43.829

Reference yield:

ethyl 3-<4-(tert-butoxycarbonyl)phenyl>-3-methylacrylate → 4-<3-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-1-methylpropyl>benzoic acid (149325-61-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / H₂ / 10percent Pd/C / ethanol

2: 98 percent / 1N NaOH / ethanol / 3 h / Ambient temperature

3: 100 percent / NaBH₄, BF₃*Et₂O / tetrahydrofuran / -78 - 20 °C

4: 22 g / triethylamine / CH₂Cl₂ / 1 h / -78 °C

5: 94 percent / NaI / acetone / 12 h / Heating

6: 18.8 percent / tributyltin hydride, azobisisobutyronitrile / benzene / Heating

7: 96 percent / N,N-diisopropylethylamine / hexane; ethanol; acetonitrile / 5 h / Ambient temperature

8: 51 percent / 2-methyl-propan-2-ol / 12 h / 160 °C

9: 100 percent / 1N HCl / acetic acid / 2 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetic acid; acetone; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.43.829

upstream raw materials:

tert-butyl 4-<3-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-1-methylpropyl>benzoate

4-acetylbenzoic acid tert-butyl ester

tert-butyl 4-(3-hydroxy-1-methylpropyl)benzoate

tert-butyl 4-(3-iodo-1-methylpropyl)benzoate

Downstream raw materials:

diethyl N-<4-<3-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-1-methylpropyl>benzoyl>-L-glutamate