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Chemistry
Heterocyclic Building Blocks
Pyrrolines
3,4-Dihydro-2H-pyrrol-5-amine
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Pyrrolines
Amines

[ CAS No. 872-34-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 872-34-4
Chemical Structure| 872-34-4
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Quality Control of [ 872-34-4 ]

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Product Details of [ 872-34-4 ]

CAS No. :872-34-4 MDL No. :MFCD11036037
Formula : C4H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 84.12 Pubchem ID :-
Synonyms :

Safety of [ 872-34-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 872-34-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 872-34-4 ]

[ 872-34-4 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 872-34-4 ]
  • [ 1852-17-1 ]
Reference： [1]Synthesis,1989,p. 443 - 444
  • 2
  • [ 872-34-4 ]
  • [ 4209-02-3 ]
  • 1-(4-Bromo-phenyl)-2-(2-imino-pyrrolidin-1-yl)-ethanone; hydrochloride [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 49 - 64
  • 3
  • [ 872-34-4 ]
  • [ 4209-25-0 ]
  • 1-(2-Chloro-phenyl)-2-(2-imino-pyrrolidin-1-yl)-ethanone; hydrochloride [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 49 - 64
  • 4
  • [ 73742-45-7 ]
  • [ 872-34-4 ]
  • [ 7440-44-0 ]
  • 5-chloro-6-[1-(2-iminopyrrolidinyl)methyl]uracil hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With sodium ethanolate; In hydrogenchloride; water; N,N-dimethyl-formamide; (2) 5-Chloro-6-chloromethyluracil (5.0 g), 2-iminopyrrolidine (6.14 g), and sodium ethoxide (5.24 g) were dissolved in N,N-dimethylformamide (50 ml) and the resultant solution was stirred for 14 hours at room temperature. Subsequently, precipitated crystals were collected through filtration, and the crystals were suspended in water (30 ml). The resultant suspension was neutralized with acetic acid and washed. Subsequently, insoluble matter was collected through filtration and was dissolved in 1N HCl (60 ml). Activated carbon was added to the resultant solution and the mixture was subjected to filtration. The filtrate was concentrated under reduced pressure, and the residue was washed with ethanol, followed by filtration, to thereby obtain 2.68 g of the title compound (38% yield). Melting Point: >=255 C. (decomposed) NMR spectral data (DMSO-d6) δ 2.04 (2H, quintet, J=7.6 Hz), 2.87 (2H, t, J=7.6 Hz), 3.59 (2H, t, J=7.6 Hz), 4.69 (2H, s), 9.40 (1H, s), 11.46 (1H, s), 11.73 (1H, s).
38% With sodium ethanolate; In hydrogenchloride; water; N,N-dimethyl-formamide; Example 6 Synthesis of 5-chloro-6-(1-(2-iminopyrrolidinyl)-methyl)uracil hydrochloride (Compound 29) A solution of 5.0 g of 5-chloro-6-chloromethyl-uracil, 6.14 g of 2-iminopyrrolidine and 5.24 g of sodium ethoxide in N,N-dimethylformamide (50 ml) was stirred at room temperature for 14 hours. A crystallized matter was collected by filtration and then suspended in 30 ml of water. After the suspension was neutralized with acetic acid and then washed, an insoluble matter was collected by filtration and then dissolved in 60 ml of 1N hydrochloric acid. Activated carbon was added to the resultant solution, followed by filtration. The filtrate was concentrated under reduced pressure, and the residue so obtained was washed with ethanol and collected with filtration, whereby 2.68 g of the title compound were obtained (yield: 38%).
38% With sodium ethanolate; In hydrogenchloride; water; N,N-dimethyl-formamide; Example 6 Synthesis of 5-chloro-6-(1-(2-iminopyrrolidinyl)-methyl)uracil hydrochloride (Compound 29) A solution of 5.0 g of <strong>[73742-45-7]5-chloro-6-chloromethyluracil</strong>, 6.14 g of 2-iminopyrrolidine and 5.24 g of sodium ethoxide in N,N-dimethylformamide (50 ml) was stirred at room temperature for 14 hours. A crystallized matter was collected by filtration and then suspended in 30 ml of water. After the suspension was neutralized with acetic acid and then washed, an insoluble matter was collected by filtration and then dissolved in 60 ml of 1 N hydrochloric acid. Activated carbon was added to the resultant solution, followed by filtration. The filtrate was concentrated under reduced pressure, and the residue so obtained was washed with ethanol and collected by filtration, whereby 2.68 g of the title compound were obtained (yield: 38%).
Reference： [1]Patent: US6479500,2002,B1
[2]Patent: US5744475,1998,A
[3]Patent: US6255314,2001,B1
  • 5
  • [ 73742-45-7 ]
  • [ 872-34-4 ]
  • 5-chloro-6-[1-(2-iminopyrrolidinyl)methyl]uracil hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With sodium ethanolate; In hydrogenchloride; water; N,N-dimethyl-formamide; A solution of 5.0 g of <strong>[73742-45-7]5-chloro-6-chloromethyluracil</strong>, 6.14 g of 2-imino pyrrolidine and 5.24 g of sodium ethoxide in 50 ml of N,N-dimethylformamide was stirred at room temperature for 14 hours. The resulting crystals were collected by filtration and suspended in 30 ml of water. The suspension was neutralized with acetic acid and washed. The insoluble substances were collected by filtration and dissolved in 60 ml of 1N hydrochloric acid. After addition of activated carbon, the resulting mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was washed with ethanol and collected by filtration, giving 2.68 g of the desired compound (yield 38%). The physical properties of this compound are as follows: mp: >=255 C. (decomp.); NMR spectrum (DMSO-d6)δ: 2.04(2H, quintet, J=7.6 Hz), 2.87(2H, t, J=7.6 Hz), 3.59(2H, t, J=7.6 Hz), 4.69(2H, s), 9.40(1H, s), 11.46(1H, s), 11.73(1H, s).
3.9 g 5-Chloro-6-chloromethyluracil (lO.Og, 0.05 mol) was suspended in DMF (100ml) at 25-30oC under nitrogen atmosphere. Thereafter 2- iminopyrrolidine (12.28 g; 0.15 mol) and sodium ethoxide (14.9 g; 0.15 mol) was added at 25-30C. The suspension was stirred for a period of 14 hrs at 25-30C then filtered the reaction mass at 25-30oC and dried under reduced pressure. The filtered solid was suspended in DM water (60ml) and neutralized with acetic acid to (pH-7.0) and stirred for lhr at 25-30C. The solid product was off and washed with DM water (10ml) .The solid was dissolved in 1NHC1 (102ml) and treated with activated charcoal at 25-30C for 15min, then filtered thorough hyflo. The filtrate concentrated under vacuum at 50-55 C to obtain solid, which was washed with ethanol (30ml) and dried under reduced pressure to obtain crystalline Tipiracil hydrochloride. (0063) Yield: 3.9g (0064) Chromatographic purity by HPLC: 99.29 (0065) Polymorph-XRPD represented as Figure 2.
Reference： [1]Patent: US6596720,2003,B1
[2]Patent: WO2019/53574,2019,A1 .Location in patent: Page/Page column 12-13
  • 6
  • [ 628-20-6 ]
  • [ 872-34-4 ]
YieldReaction ConditionsOperation in experiment
74% With ammonia; In ethanol; at 100 - 120℃; for 10h;Sealed tube; 1L three-necked flask 600ml of anhydrous ethanol under ice four hours continuously fed ammonia to saturation;pressurized cylinders ethanol was added a saturated solution of ammonia had been prepared, and then added 103.5g <strong>[628-20-6]4-chlorobutyronitrile</strong> (lmol), sealed in an oil bath heated 100-120 C, 10 hours;After completion of the reaction, cooled to room temperature, the reaction solution was spin to 70% ethanol, the precipitated solid was filtered, and the mother liquor was recrystallized with ether to give a solid, solids were combined to give a pale yellow solid drying 89.2g,No. HHC-014-A, Yield 74%
Reference： [1]Patent: CN103435617,2016,B .Location in patent: Paragraph 0020-0022
  • 7
  • [ 155272-73-4 ]
  • [ 872-34-4 ]
  • [ 623564-38-5 ]
YieldReaction ConditionsOperation in experiment
28% 9.64g (80mmol) HCC-014-A is added to the IL-port bottle, 350ml ethanol was added to dissolve;added with stirring 15.43g28% (80mmol) of methanol solution of sodium methoxide;the addition was complete stirring 5min;at room temperature, rapid dropwise 17g (88mmol) HCC-014-B in absolute ethanol (IOOml) solution;I hour stirring at room temperature;spin dry ethanol, was added 350ml of chloroform, 8.08g (80mmol) of triethylamine, heated at reflux for 2.5-3 hours TLC (may be sampled every half hour the reaction was monitored conditions);spin dry solvent, column chromatography (acetone: chloroform = 1: 2) to give a pale yellow solid 3.05g, yield 28%, such as to give the product a darker, available active carbon purification.
Reference： [1]Patent: CN103435617,2016,B .Location in patent: Paragraph 0024-0030
  • 8
  • [ 73742-45-7 ]
  • [ 872-34-4 ]
  • Tipiracil [ No CAS ]
YieldReaction ConditionsOperation in experiment
38.2% With sodium ethanolate; In N,N-dimethyl-formamide; at 20℃; for 14h; 2)Chloro-6-chloromethyluracil (5.0 g), 2-iminopyrrolidine (6.14 g) and sodium ethoxide (5.24 g) were added to a solution of50ml DMF solution,Stirring at room temperature for 14h,filter,The solid was added to 30 ml of water,After neutralization with acetic acid and washing,Filter.The solid obtained by filtration was dissolved in 1N hydrochloric acid and activated charcoal was added followed by suction filtration.The filtrate was depressurized to give 2.68 g of solid,Yield 38.2%;The total yield was 35.1%;Purity 98.7%.
Reference： [1]Patent: CN106749194,2017,A .Location in patent: Paragraph 0045

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