4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid supplier

Name
4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid
EINECS 429-790-9
CAS No. 137281-39-1
Article Data18
CAS DataBase
Density 1.559 g/cm³
Solubility
Melting Point > 270 °C
Formula C₁₅H₁₄N₄O₃
Boiling Point 609.183 °C at 760 mmHg
Molecular Weight 298.301
Flash Point 322.223 °C
Transport Information
Appearance pale pink solid
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms Benzoicacid, 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]-(9CI);1H-Pyrrolo[2,3-d]pyrimidine, benzoic acid deriv.;
PSA 124.86000
LogP 1.89800

Synthetic route

: 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid methyl ester

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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%

: 229470-22-8
4-[3-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-4-nitrobutyl]benzoic acid ethyl ester

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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%

: 4-(3-bromo-4-oxobutyl)benzoic acid methyl ester

: 56-06-4
2,6-diaminopyrimidin-4-ol

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

Conditions	Yield
With sodium acetate In methanol; water at 50 - 55℃; for 5h; Inert atmosphere;	75%

: N-[4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]-benzoyl]-L-glutamic acid disodium salt

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

Conditions	Yield
With hydrogenchloride; water at 100℃; for 120h;	37%
With hydrogenchloride; water at 100℃; for 120h;	37%

: 146943-41-1
4-[3-(2,4-Diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-4,4-dimethoxy-butyl]-benzoic acid tert-butyl ester

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

Conditions	Yield
With water; trifluoroacetic acid

: 151864-81-2
ethyl 4-(3-oxopropyl)benzoate

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 259145-25-0
4-(3-hydroxy-4-nitrobutyl)benzoic acid ethyl ester

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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-(4-nitrobut-3-enyl)benzoic acid ethyl ester

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 51934-41-9
4-iodobenzoic acid ethyl ester

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 229470-21-7
4-((E)-4-Nitro-but-3-enyl)-benzoic acid ethyl ester

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / ethyl acetate; H2O / 24 h / 50 °C 2: 57 percent View Scheme

: 65874-27-3
4-(tert-butoxycarbonyl)benzaldehyde

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

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

: 126931-32-6
tert-Butyl 4-(3-hydroxy-1-propyl)benzoate

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 134372-99-9
3-(4-<2,2-dimethylethyl>carboxyphenyl)-1-propanal

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 134373-00-5
tert-butyl 4-(4-methoxy-3-butenyl)benzoate

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 146943-27-3
methyl 3-<4-(tert-butoxycarbonyl)phenyl>propenoate

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

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

: 126931-31-5
methyl 3-<4-(tert-butoxycarbonyl)phenyl>propanoate

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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-(4-Cyano-3-dimethoxymethyl-4-ethoxycarbonyl-butyl)-benzoic acid tert-butyl ester

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 106200-41-3
4-(4-carbomethoxyphenyl)butanal

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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-(3-bromo-4-oxobutyl)benzoic acid methyl ester

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 123910-86-1
4-(4-hydroxy-1-butynyl)benzoic acid methyl ester

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 619-42-1
4-methoxycarbonylphenyl bromide

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 123910-88-3
methyl 4-(4-hydroxybut-1-yl)benzoate

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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-(4-carboxymethoxyphenyl)butanal sodium bisulfite adduct

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 72313-37-2
ethyl 4-(3-formylpropyl)benzoate

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 927897-33-4
ethyl 4-(3-bromo-4-oxobutyl)benzoate

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 151864-75-4
ethyl 4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl)benzoate

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 40 - 50℃; for 24h; Inert atmosphere;

: 619-44-3
methyl 4-iodobenzoate

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

Conditions

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

: 108-24-7
acetic anhydride

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 4-[2-(2-acetylamino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid

Conditions

Conditions	Yield
With acetic acid at 50℃; for 1h; Temperature;	97.1%
With acetic acid at 30 - 50℃; for 1h; Temperature;	97.1%

: 100-44-7
benzyl chloride

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 4-[2-(2-benzylamino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid

Conditions

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;

: 98-59-9
p-toluenesulfonyl chloride

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 4-[2-(2-(p-tolylsulfonyl)amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid

Conditions

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;

: 76-83-5
trityl chloride

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 4-[2-(2-triphenylmethylamino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid

Conditions

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;

: 1118-89-4
diethyl-L-glutamate hydrochloride

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 146943-43-3
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

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;

: 31329-64-3
3,5-dimethylisoxazol-4-amine

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)-N-(3,5-dimethylisoxazol-4-yl)benzamide

Conditions

Conditions	Yield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere;	93%

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 146943-43-3
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

: C39H41N9O8

Conditions

Conditions	Yield
With triethylamine; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 25 - 30℃; for 2h; Temperature; Reagent/catalyst; Solvent;	92.6%

: 156-41-2
4-chlorophenylethylamine

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)-N-(4-chlorophenethyl)benzamide

Conditions

Conditions	Yield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere;	92%

: 96-50-4
2-thiazolylamine

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)-N-(thiazol-2-yl)benzamide

Conditions

Conditions	Yield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere;	91%

: 23150-65-4
L-glutamic dimethyl ester hydrochloride

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: dipotassium (S)-2-(4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido) pentanedioate

Conditions

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%

: 1011-15-0
1-(o-fluorophenyl)piperazine

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 2-amino-5-(4-(4-(2-fluorophenyl)piperazine-1-carbonyl)phenethyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

Conditions

Conditions	Yield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere;	90%

: 4318-37-0
1-Methylhomopiperazine

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 2-amino-5-(4-(4-methyl-1,4-diazepane-1-carbonyl)phenethyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

Conditions

Conditions	Yield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere;	89%

: 2706-56-1
2-(aminoethyl)pyridine

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)-N-(2-(pyridin-2-yl)ethyl)benzamide

Conditions

Conditions	Yield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere;	88%

: 109-02-4
4-methyl-morpholine

: 3140-73-6
2-chloro-4,6-dimethoxy-1 ,3,5-triazine

: 1118-89-4
diethyl-L-glutamate hydrochloride

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

A: 146943-43-3
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

B: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-morpholine

Conditions

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%

...Expand

: 104-15-4
toluene-4-sulfonic acid

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: (R)-2-aminoglutaric acid diethyl ester hydrochloride

: C24H29N5O6*C7H8O3S

Conditions

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%

...Expand

: 27578-60-5
1-(2-aminoethyl)piperidine

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)-N-(2-(piperidin-1-yl)ethyl)benzamide

Conditions

Conditions	Yield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere;	84%

: 118252-57-6
L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-glutamic acid heptakis-t-butyl ester

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: C73H112N10O21

Conditions

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%

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%

: 23150-65-4
L-glutamic dimethyl ester hydrochloride

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 155405-81-5
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

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%

: 917560-78-2
(S)-1-(pyrrolidin-3-yl)piperidine

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: (S)-2-amino-5-(4-(3-(piperidin-1-yl)pyrrolidine-1-carbonyl)phenethyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

Conditions

Conditions	Yield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere;	78%

: 1376616-07-7
(S)-benzyl 5-acetoxy-4-aminopentanoate

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 1376616-08-8
(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

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%

: 17430-98-7
[(1S)-1-cyclohexylethyl]amine

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: (S)-4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)-N-(1-cyclohexylethyl)benzamide

Conditions

Conditions	Yield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere;	72%

: 1583-88-6
4-fluoro-2-phenethylamine

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)-N-(4-fluorophenethyl)benzamide

Conditions

Conditions	Yield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0.1℃; for 3.25h; Inert atmosphere;	71%

: 1207601-67-9
amine SDC-TRAP-0004

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)-N-(2-(5-(3-(2,4-dihydroxy-5-isopropylphenyl)-5-hydroxy-4H-1,2,4-triazol-4-yl)-1H-indol-1-yl)ethyl)-N-methylbenzamide

Conditions

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%

: 1207601-67-9
amine SDC-TRAP-0004

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)-N-(2-(5-(3-(2,4-dihydroxy-5-isopropylphenyl)-5-hydroxy-4H-1,2,4-triazol-4-yl)-1H-indol-1-yl)ethyl)-N-methylbenzamide

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 18h;	70%

: 1118-89-4
diethyl-L-glutamate hydrochloride

: 104-15-4
toluene-4-sulfonic acid

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: 165049-28-5
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

...Expand

: 1118-89-4
diethyl-L-glutamate hydrochloride

: 104-15-4
toluene-4-sulfonic acid

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: (2R)-2-[[4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid diethyl ester p-toluenesulfonate

Conditions

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%

...Expand

: C10H21NO4Si

: 137281-39-1
4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

: C25H33N5O6Si

Conditions

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%

4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid Chemical Properties

Molecular Structure of Benzoic acid,4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]- (CAS NO.137281-39-1):

Systematic Name: 4-[2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid
SMILES: O=C(O)c1ccc(cc1)CCc2cnc3N\C(=N/C(=O)c23)N
InChI: InChI=1/C15H14N4O3/c16-15-18-12-11(13(20)19-15)10(7-17-12)6-3-8-1-4-9(5-2-8)14(21)22/h1-2,4-5,7H,3,6H2,(H,21,22)(H4,16,17,18,19,20)
InChIKey: AIZPFZIKHIJCQX-UHFFFAOYAO
Empirical Formula: C₁₅H₁₄N₄O₃
Molecular Weight: 298.2967
Nominal Mass: 298 Da
Average Mass: 298.2967 Da
Monoisotopic Mass: 298.10659 Da
H bond acceptors: 7
H bond donors: 5
Freely Rotating Bonds: 4
Index of Refraction: 1.746
Molar Refractivity: 77.659 cm³
Molar Volume: 191.311 cm³
Surface Tension: 69.594 dyne/cm
Density: 1.559 g/cm³
Flash Point: 322.223 °C
Enthalpy of Vaporization: 95.15 kJ/mol
Boiling Point: 609.183 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25 °C
Appearance: Pale Pink Solid
Melting Point: >270 °C (dec.)
Product Categories: Organic acids; PEMETREXED DISODIUM; (intermediate of pemetrexed); Various Intermediates; Intermediates; Intermediates & Fine Chemicals; Pharmaceuticals

4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid Uses

Benzoic acid,4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]- (CAS NO.137281-39-1) is used as pemetrexed intermediate.

4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid Specification

Benzoic acid,4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]- (CAS NO.137281-39-1), its Synonyms are Benzoicacid, 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]-(9CI) ; 1H-Pyrrolo[2,3-d]pyrimidine, benzoic acid deriv. ; 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid .

Product Name

4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid

Synthetic route

4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid Chemical Properties

4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid Uses

4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid Specification

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