Product: Pemetrexed Disodium Intermediate Name 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrol[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid Molecular Formula C15H14N4O3 Molecular Weight 298.30
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inquiryProName: 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pym... CasNo: 137281-39-1 Molecular Formula: C15H14N4O3 Appearance: detailed see specifications Application: It is an important raw material and in... DeliveryTime: prompt PackAge: according to the
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inquiryItems Standard Result Assay 98%min ---------------------------------------------------------------------------------------------
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inquiryUnique advantages Guaranteed purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:White powder Storage:cool dry place Package:1kg/foil bag;25kg/drum Application:pharmaceutical intermediate Transpo
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inquiryName:4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid CAS NO: 137281-39-1 Grade:Medical scientific research and export Molecular formula:C15H14N4O3 Molecular weight:298.2967 Product Quality 12 years of chemica
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inquiryProduct Description Product website: http://www.finerchem.com/pro01en/id/844.html Product Name 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrol[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid
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inquiryTIANFUCHEM--137281-39-1 -- 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid in stock Our company was built in 2009 with an ISO certificate.In the past 10 years, we have grown up as a famous fine chemicals supp
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inquiryAdvantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&
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inquiry1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:White Crystalline Solid Storage:Store in sealed contai
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inquiryProduct Name: 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid CAS: 137281-39-1 MF: C15H14N4O3 MW: 298.3 EINECS: 429-790-9 Mol File: 137281-39-1.mol 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]py
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inquiry4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid CAS:137281-39-1 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chem
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inquiryHello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai
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inquiry4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrim CAS: 137281-39-1 Specification Test Items Specifications Result Appearance White to off-white powder Off-white powder
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inquiryHenan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod
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inquiryBest quality & Attractive price & Professional service; Trial & Pilot & Commercial Hisunny Chemical is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality intermediates, specia
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inquiryAppearance:off-white to white solid Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for Synthesis API and Research Transportation:By Sea/Air/Courier Port:Qingdao
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inquiryOur Services 1. New Molecules R&D 2. Own test center HPLC NMR GC LC-MS 3. API and Intermediates from China reputed manufacturers 4. Documents support COA MOA MSDS DMF open part Our advantages 1. Government awarded company. Top 100 enter
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inquiry4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide at 40℃; for 1h; | 100% |
With sodium hydroxide In water at 40℃; for 1.5h; Large scale; | 91% |
With ethanol at 40℃; for 3h; Molecular sieve; Industrial scale; | 85.1% |
4-[3-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-4-nitrobutyl]benzoic acid ethyl ester
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide; sulfuric acid; acetic acid In water; ethyl acetate | 98% |
Multistep reaction; | 57% |
Stage #1: 4-[3-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-4-nitrobutyl]benzoic acid ethyl ester With sodium hydroxide at 20℃; for 2h; Stage #2: With sulfuric acid at 0℃; for 3h; Nef reaction; Stage #3: With sodium hydroxide at 20℃; for 1h; pH=7; | 57% |
2,6-diaminopyrimidin-4-ol
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With sodium acetate In methanol; water at 50 - 55℃; for 5h; Inert atmosphere; | 75% |
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; water at 100℃; for 120h; | 37% |
With hydrogenchloride; water at 100℃; for 120h; | 37% |
4-[3-(2,4-Diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-4,4-dimethoxy-butyl]-benzoic acid tert-butyl ester
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With water; trifluoroacetic acid |
ethyl 4-(3-oxopropyl)benzoate
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 68 percent / aq. NaOH / ethanol / 48 h / 38 °C 2.1: 90 percent / CH3SO2Cl; Et3N / CH2Cl2 / 0 - 20 °C 3.1: 91 percent / H2O; ethyl acetate / 24 h / 50 °C 4.1: aq. NaOH / 2 h / 20 °C 4.2: aq. H2SO4 / 3 h / 0 °C 4.3: 57 percent / aq. NaOH / 1 h / 20 °C / pH 7 View Scheme | |
Multi-step reaction with 4 steps 1: 72 percent / NaOH / ethanol 2: 90 percent / CH3SO2Cl; Et3N 3: 91 percent / ethyl acetate; H2O / 24 h / 50 °C 4: 57 percent View Scheme |
4-(3-hydroxy-4-nitrobutyl)benzoic acid ethyl ester
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 90 percent / CH3SO2Cl; Et3N / CH2Cl2 / 0 - 20 °C 2.1: 91 percent / H2O; ethyl acetate / 24 h / 50 °C 3.1: aq. NaOH / 2 h / 20 °C 3.2: aq. H2SO4 / 3 h / 0 °C 3.3: 57 percent / aq. NaOH / 1 h / 20 °C / pH 7 View Scheme | |
Multi-step reaction with 3 steps 1: 90 percent / CH3SO2Cl; Et3N 2: 91 percent / ethyl acetate; H2O / 24 h / 50 °C 3: 57 percent View Scheme |
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 91 percent / H2O; ethyl acetate / 24 h / 50 °C 2.1: aq. NaOH / 2 h / 20 °C 2.2: aq. H2SO4 / 3 h / 0 °C 2.3: 57 percent / aq. NaOH / 1 h / 20 °C / pH 7 View Scheme |
4-iodobenzoic acid ethyl ester
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 98 percent / Pd(OAc)2 2: 72 percent / NaOH / ethanol 3: 90 percent / CH3SO2Cl; Et3N 4: 91 percent / ethyl acetate; H2O / 24 h / 50 °C 5: 57 percent View Scheme | |
Multi-step reaction with 4 steps 1: lithium chloride; lithium acetate; tetrabutyl-ammonium chloride; palladium diacetate / N,N-dimethyl-formamide / 3 h / 70 °C 2: 2,2-dimethyl-5,5-dibromo-1,3-dioxane-4,6-dione; hydrogenchloride / diethyl ether / 24 h / 20 °C 3: sodium acetate / water; methanol / 3 h / 45 °C 4: sodium hydroxide / methanol / 24 h / 40 - 50 °C / Inert atmosphere View Scheme |
4-((E)-4-Nitro-but-3-enyl)-benzoic acid ethyl ester
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 91 percent / ethyl acetate; H2O / 24 h / 50 °C 2: 57 percent View Scheme |
4-(tert-butoxycarbonyl)benzaldehyde
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 94 percent / toluene / 1 h / Heating 2: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / 4 h 3: 99 percent / LiBH4 / diethyl ether / 15 h / Ambient temperature 4: 87 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -60 °C 5: 1) t-BuOK / 1) THF, toluene, 10 min, 2) toluene, 0 deg C, 20 min 6: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 7: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 8: CF3COOH, H2O View Scheme |
tert-Butyl 4-(3-hydroxy-1-propyl)benzoate
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 87 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -60 °C 2: 1) t-BuOK / 1) THF, toluene, 10 min, 2) toluene, 0 deg C, 20 min 3: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 4: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 5: CF3COOH, H2O View Scheme |
3-(4-<2,2-dimethylethyl>carboxyphenyl)-1-propanal
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1) t-BuOK / 1) THF, toluene, 10 min, 2) toluene, 0 deg C, 20 min 2: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 3: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 4: CF3COOH, H2O View Scheme |
tert-butyl 4-(4-methoxy-3-butenyl)benzoate
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 2: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 3: CF3COOH, H2O View Scheme |
methyl 3-<4-(tert-butoxycarbonyl)phenyl>propenoate
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / 4 h 2: 99 percent / LiBH4 / diethyl ether / 15 h / Ambient temperature 3: 87 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -60 °C 4: 1) t-BuOK / 1) THF, toluene, 10 min, 2) toluene, 0 deg C, 20 min 5: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 6: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 7: CF3COOH, H2O View Scheme |
methyl 3-<4-(tert-butoxycarbonyl)phenyl>propanoate
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 99 percent / LiBH4 / diethyl ether / 15 h / Ambient temperature 2: 87 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -60 °C 3: 1) t-BuOK / 1) THF, toluene, 10 min, 2) toluene, 0 deg C, 20 min 4: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 5: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 6: CF3COOH, H2O View Scheme |
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 2: CF3COOH, H2O View Scheme |
4-(4-carbomethoxyphenyl)butanal
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 5,5-dibromobarbituric acid; hydrogen bromide; acetic acid / dichloromethane / 25 °C / Large scale 2: sodium acetate / water; acetonitrile / 3 h / 40 °C / Large scale 3: sodium hydroxide / water / 1.5 h / 40 °C / Large scale View Scheme | |
Multi-step reaction with 3 steps 1: hydrogen bromide; acetic acid; bromine / ethyl acetate / 1 h / 0 °C 2: sodium acetate / water; acetonitrile / 3.5 h / 40 °C 3: sodium hydroxide; water / 1 h / 40 °C View Scheme | |
Multi-step reaction with 3 steps 1: bromine / acetonitrile / 2 h / 0 - 20 °C 2: sodium acetate 3: sodium hydroxide; water View Scheme | |
Multi-step reaction with 3 steps 1: pyridinium hydrobromide perbromide / acetonitrile / 0.17 h / -5 - 5 °C 2: sodium acetate; sodium hydrogensulfite / water / 2 h / 40 °C 3: sodium hydroxide; water / 2 h / 40 °C View Scheme | |
Multi-step reaction with 3 steps 1: acetic acid; 5,5-dibromobarbituric acid; hydrogen bromide / dichloromethane / 16 h / 20 °C 2: sodium acetate / acetonitrile; water / 3 h / 40 °C 3: sodium hydroxide / 1.5 h / 40 °C View Scheme |
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium acetate / water; acetonitrile / 3 h / 40 °C / Large scale 2: sodium hydroxide / water / 1.5 h / 40 °C / Large scale View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium acetate 2.1: sodium hydroxide 2.2: 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium acetate / water; acetonitrile / 3.5 h / 40 °C 2: sodium hydroxide; water / 1 h / 40 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium acetate 2: sodium hydroxide; water View Scheme | |
Multi-step reaction with 2 steps 1: sodium acetate / acetonitrile; water / 3 h / 40 °C 2: sodium hydroxide / 1.5 h / 40 °C View Scheme |
4-(4-hydroxy-1-butynyl)benzoic acid methyl ester
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: hydrogen; 5%-palladium/activated carbon / dichloromethane / 3.5 h / 3345.86 Torr / Inert atmosphere; Autoclave; Large scale 2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / -10 - 20 °C / pH 9.5 / Large scale 3: 5,5-dibromobarbituric acid; hydrogen bromide; acetic acid / dichloromethane / 25 °C / Large scale 4: sodium acetate / water; acetonitrile / 3 h / 40 °C / Large scale 5: sodium hydroxide / water / 1.5 h / 40 °C / Large scale View Scheme | |
Multi-step reaction with 4 steps 1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 5 h / 25 - 30 °C / 6464.52 Torr / Inert atmosphere 2: potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / water; dichloromethane / 0.5 h / 25 - 30 °C / Inert atmosphere 3: pyridinium hydrobromide perbromide / tert-butyl methyl ether / 8 h / 25 - 30 °C / Inert atmosphere 4: sodium acetate / water; methanol / 5 h / 50 - 55 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: palladium 10% on activated carbon; hydrogen / dichloromethane / 30 °C / 37503.8 Torr / Flow reactor 2: sodium acetate; pyridinium chlorochromate / dichloromethane / 5 h / 20 °C 3: acetic acid; 5,5-dibromobarbituric acid; hydrogen bromide / dichloromethane / 16 h / 20 °C 4: sodium acetate / acetonitrile; water / 3 h / 40 °C 5: sodium hydroxide / 1.5 h / 40 °C View Scheme |
4-methoxycarbonylphenyl bromide
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: palladium dichloride; triphenylphosphine; copper(l) iodide; diethylamine / ethyl acetate / 4 h / 50 °C / Large scale 2: hydrogen; 5%-palladium/activated carbon / dichloromethane / 3.5 h / 3345.86 Torr / Inert atmosphere; Autoclave; Large scale 3: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / -10 - 20 °C / pH 9.5 / Large scale 4: 5,5-dibromobarbituric acid; hydrogen bromide; acetic acid / dichloromethane / 25 °C / Large scale 5: sodium acetate / water; acetonitrile / 3 h / 40 °C / Large scale 6: sodium hydroxide / water / 1.5 h / 40 °C / Large scale View Scheme | |
Multi-step reaction with 4 steps 1: lithium acetate; lithium chloride; tetrabutyl-ammonium chloride; palladium diacetate / N,N-dimethyl-formamide / 75 °C / Inert atmosphere 2: hydrogen bromide; acetic acid; bromine / ethyl acetate / 1 h / 0 °C 3: sodium acetate / water; acetonitrile / 3.5 h / 40 °C 4: sodium hydroxide; water / 1 h / 40 °C View Scheme | |
Multi-step reaction with 5 steps 1: triethylamine; copper(l) iodide; triphenylphosphine; palladium dichloride / 3 h / 75 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 5 h / 25 - 30 °C / 6464.52 Torr / Inert atmosphere 3: potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / water; dichloromethane / 0.5 h / 25 - 30 °C / Inert atmosphere 4: pyridinium hydrobromide perbromide / tert-butyl methyl ether / 8 h / 25 - 30 °C / Inert atmosphere 5: sodium acetate / water; methanol / 5 h / 50 - 55 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1: lithium acetate; lithium chloride; tetrabutylammomium bromide; palladium diacetate / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 2: pyridinium hydrobromide perbromide / acetonitrile / 0.17 h / -5 - 5 °C 3: sodium acetate; sodium hydrogensulfite / water / 2 h / 40 °C 4: sodium hydroxide; water / 2 h / 40 °C View Scheme | |
Multi-step reaction with 6 steps 1: triphenylphosphine; palladium dichloride; copper(l) iodide; diethylamine / ethyl acetate / 4 h / 50 °C 2: palladium 10% on activated carbon; hydrogen / dichloromethane / 30 °C / 37503.8 Torr / Flow reactor 3: sodium acetate; pyridinium chlorochromate / dichloromethane / 5 h / 20 °C 4: acetic acid; 5,5-dibromobarbituric acid; hydrogen bromide / dichloromethane / 16 h / 20 °C 5: sodium acetate / acetonitrile; water / 3 h / 40 °C 6: sodium hydroxide / 1.5 h / 40 °C View Scheme |
methyl 4-(4-hydroxybut-1-yl)benzoate
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / -10 - 20 °C / pH 9.5 / Large scale 2: 5,5-dibromobarbituric acid; hydrogen bromide; acetic acid / dichloromethane / 25 °C / Large scale 3: sodium acetate / water; acetonitrile / 3 h / 40 °C / Large scale 4: sodium hydroxide / water / 1.5 h / 40 °C / Large scale View Scheme | |
Multi-step reaction with 3 steps 1: potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / water; dichloromethane / 0.5 h / 25 - 30 °C / Inert atmosphere 2: pyridinium hydrobromide perbromide / tert-butyl methyl ether / 8 h / 25 - 30 °C / Inert atmosphere 3: sodium acetate / water; methanol / 5 h / 50 - 55 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1: sodium acetate; pyridinium chlorochromate / dichloromethane / 5 h / 20 °C 2: acetic acid; 5,5-dibromobarbituric acid; hydrogen bromide / dichloromethane / 16 h / 20 °C 3: sodium acetate / acetonitrile; water / 3 h / 40 °C 4: sodium hydroxide / 1.5 h / 40 °C View Scheme |
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: chloro-trimethyl-silane; bromine 2.1: sodium acetate 3.1: sodium hydroxide 3.2: 0 °C View Scheme |
ethyl 4-(3-formylpropyl)benzoate
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 2,2-dimethyl-5,5-dibromo-1,3-dioxane-4,6-dione; hydrogenchloride / diethyl ether / 24 h / 20 °C 2: sodium acetate / water; methanol / 3 h / 45 °C 3: sodium hydroxide / methanol / 24 h / 40 - 50 °C / Inert atmosphere View Scheme |
ethyl 4-(3-bromo-4-oxobutyl)benzoate
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium acetate / water; methanol / 3 h / 45 °C 2: sodium hydroxide / methanol / 24 h / 40 - 50 °C / Inert atmosphere View Scheme |
ethyl 4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl)benzoate
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 40 - 50℃; for 24h; Inert atmosphere; |
methyl 4-iodobenzoate
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: palladium diacetate; lithium chloride; lithium acetate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 10 h / 60 °C / Inert atmosphere 2: bromine / acetonitrile / 2 h / 0 - 20 °C 3: sodium acetate 4: sodium hydroxide; water View Scheme |
acetic anhydride
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With acetic acid at 50℃; for 1h; Temperature; | 97.1% |
With acetic acid at 30 - 50℃; for 1h; Temperature; | 97.1% |
benzyl chloride
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 30 - 60℃; for 1h; Temperature; | 96.9% |
With triethylamine In N,N-dimethyl-formamide at 30 - 50℃; for 1h; Temperature; |
p-toluenesulfonyl chloride
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 0 - 5℃; for 1h; | 96.7% |
With triethylamine In N,N-dimethyl-formamide at 0 - 30℃; for 1h; |
trityl chloride
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 30 - 35℃; for 1h; | 96.3% |
With triethylamine In N,N-dimethyl-formamide at 30 - 35℃; for 1h; |
diethyl-L-glutamate hydrochloride
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester
Conditions | Yield |
---|---|
With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; sodium hydroxide In ethanol; water at 40℃; for 3h; | 94.5% |
With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine at 20℃; Condensation; | 62% |
Stage #1: 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: diethyl-L-glutamate hydrochloride With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 3.5h; | 62% |
With 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; 4-methylmorpholine N-oxide In N,N-dimethyl-formamide at 25℃; for 1.5h; Large scale; | |
With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 6h; |
3,5-dimethylisoxazol-4-amine
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere; | 93% |
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester
Conditions | Yield |
---|---|
With triethylamine; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 25 - 30℃; for 2h; Temperature; Reagent/catalyst; Solvent; | 92.6% |
4-chlorophenylethylamine
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere; | 92% |
2-thiazolylamine
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere; | 91% |
L-glutamic dimethyl ester hydrochloride
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Stage #1: 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 0 - 30℃; Inert atmosphere; Stage #2: L-glutamic dimethyl ester hydrochloride In N,N-dimethyl-formamide at 0 - 5℃; Stage #3: With potassium hydroxide In dichloromethane; water for 1.5h; | 90.38% |
1-(o-fluorophenyl)piperazine
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere; | 90% |
1-Methylhomopiperazine
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere; | 89% |
2-(aminoethyl)pyridine
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere; | 88% |
4-methyl-morpholine
2-chloro-4,6-dimethoxy-1 ,3,5-triazine
diethyl-L-glutamate hydrochloride
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
A
N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester
Conditions | Yield |
---|---|
Stage #1: 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid In N,N-dimethyl-formamide at 20℃; for 1h; Cooling with ice; Inert atmosphere; Stage #2: diethyl-L-glutamate hydrochloride In N,N-dimethyl-formamide at 35℃; for 2h; Inert atmosphere; | A 85.5% B 4% |
toluene-4-sulfonic acid
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Stage #1: (R)-2-aminoglutaric acid diethyl ester hydrochloride With sodium hydrogencarbonate In water at 20℃; for 0.5h; Stage #2: toluene-4-sulfonic acid; 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In dichloromethane at 0 - 50℃; for 3h; | 85% |
1-(2-aminoethyl)piperidine
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere; | 84% |
L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-glutamic acid heptakis-t-butyl ester
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Stage #1: 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 10 - 20℃; for 0.5h; Large scale; Stage #2: L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-glutamic acid heptakis-t-butyl ester In N,N-dimethyl-formamide at 20℃; for 20h; Large scale; | 82.5% |
L-glutamic dimethyl ester hydrochloride
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic dimethyl ester
Conditions | Yield |
---|---|
Stage #1: 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; Stage #2: L-glutamic dimethyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; | 80.4% |
Stage #1: 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 0 - 5℃; for 1.5h; Stage #2: L-glutamic dimethyl ester hydrochloride In N,N-dimethyl-formamide at 0 - 30℃; | 65.5% |
(S)-1-(pyrrolidin-3-yl)piperidine
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere; | 78% |
(S)-benzyl 5-acetoxy-4-aminopentanoate
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
(S)-benzyl 5-acetoxy-4-(4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanoate
Conditions | Yield |
---|---|
Stage #1: 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 3h; Stage #2: (S)-benzyl 5-acetoxy-4-aminopentanoate With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; | 77% |
Stage #1: 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 3h; Stage #2: (S)-benzyl 5-acetoxy-4-aminopentanoate With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; | 77% |
[(1S)-1-cyclohexylethyl]amine
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere; | 72% |
4-fluoro-2-phenethylamine
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere; | 71% |
amine SDC-TRAP-0004
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With 1,2-dichloro-ethane In N,N-dimethyl-formamide at 20℃; for 18h; | 70% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 18h; | 70% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 18h; | 70% |
amine SDC-TRAP-0004
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 18h; | 70% |
diethyl-L-glutamate hydrochloride
toluene-4-sulfonic acid
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester 4-methylbenzenesulfonic acid salt
Conditions | Yield |
---|---|
Stage #1: diethyl-L-glutamate hydrochloride; 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Industrial scale; Stage #2: toluene-4-sulfonic acid In ethanol; N,N-dimethyl-formamide at 70℃; Temperature; Inert atmosphere; Industrial scale; | 68.1% |
Stage #1: 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 50 - 60℃; for 2h; Stage #2: diethyl-L-glutamate hydrochloride With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 3.5h; Stage #3: toluene-4-sulfonic acid In ethanol for 1h; Reflux; | 55.4 g |
diethyl-L-glutamate hydrochloride
toluene-4-sulfonic acid
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Stage #1: 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In dichloromethane; N,N-dimethyl-formamide at 38 - 40℃; for 2h; Stage #2: diethyl-L-glutamate hydrochloride In dichloromethane; N,N-dimethyl-formamide for 2h; Stage #3: toluene-4-sulfonic acid In ethanol for 2h; Reflux; | 66% |
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid
Conditions | Yield |
---|---|
Stage #1: 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: C10H21NO4Si In N,N-dimethyl-formamide at 20℃; for 3h; | 64% |
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