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Basic Information
CAS No.: 137281-39-1
Name: 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid
Article Data: 18
Molecular Structure:
Molecular Structure of 137281-39-1 (4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pymol[2,3-d]pyrimodin-5-yl)ethyl]benzoic acid)
Formula: C15H14N4O3
Molecular Weight: 298.301
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.;
EINECS: 429-790-9
Density: 1.559 g/cm3
Melting Point: > 270 °C
Boiling Point: 609.183 °C at 760 mmHg
Flash Point: 322.223 °C
Appearance: pale pink solid
Risk Codes: 36/37/38
Safety: 26-36/37/39
PSA: 124.86000
LogP: 1.89800
Related products
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
ConditionsYield
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
ConditionsYield
With sodium hydroxide; sulfuric acid; acetic acid In water; ethyl acetate98%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / ethyl acetate; H2O / 24 h / 50 °C
2: 57 percent
View Scheme
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  • Best Quality 4-[2-(2-Amino-4,7-Dihydro-4-Oxo-1H-Pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]Benzoic Acid

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    Best Quality 4-[2-(2-Amino-4,7-Dihydro-4-Oxo-1H-Pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]Benzoic Acid

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    Product name: 4-[2-(2-Amino-4,7-Dihydro-4-Oxo-1H-Pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]Benzoic Acid CAS No.：137281-39-1 Molecule Formula：C15H14N4O3 Molecule Weight：298.30 Purity: 99.0% Package: 25kg/drum Description：Light yellow to off-whi

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  • 2-Amino-4,7-dihydro-5-[2-[4-(carboxy)phenyl]ethyl]-4-oxo-3H-pyrrolo[2,3-d]pyrimidine

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    2-Amino-4,7-dihydro-5-[2-[4-(carboxy)phenyl]ethyl]-4-oxo-3H-pyrrolo[2,3-d]pyrimidine

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Chemistry

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

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.

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 .