35691-20-4|2-Chloro-4-(pyrrolidin-1-yl)pyrimidine| Ambeed

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Quality Control of [ 35691-20-4 ] Purity: 98% SDS Specification

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NMR

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Product Details of [ 35691-20-4 ]

CAS No. :	35691-20-4
Formula :	C₈H₁₀ClN₃
M.W :	183.64
SMILES Code :	ClC1=NC=CC(N2CCCC2)=N1
MDL No. :	MFCD09475891
InChI Key :	OSBZWNGXKCNMHM-UHFFFAOYSA-N
Pubchem ID :	10773821

Safety of [ 35691-20-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 35691-20-4 ]

* 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 [ 35691-20-4 ]

[ 35691-20-4 ] Synthesis Path-Downstream 1~35

1
[ 123-75-1 ]
[ 3934-20-1 ]
[ 35691-20-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine; In ethanol; at 20℃; for 0.25h;	General procedure: To a solution of absolute ethanol (5 mL) and dichlorodiazine (3.36 mmol) in a 50mL round-bottom flaskwas added triethylamine (5.03 mmol), followed by the amine (5.03 mmol). The mixture was stirred either under reflux of ethanol (for dichloropyridazine and for dichloropyrazine) or at room temperature (for dichloropyrimidines). The reaction was monitored by GC. Once the starting dichlorodiazinewas completely consumed, the mixture was poured into a saturated NH4Cl solution (20 mL), then extracted with CH2Cl2 (320 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated under vacuum. The crude solid was triturated in petroleum ether, filtered through a Buchner to afford the pure product.
70%	In ethanol; at 20℃; for 12h;	General procedure: To a stirred solution of 2,4-dichloropyrimidine in EtOH was added a solution of the corresponding amine (1.2 equiv) in EtOH. After stirring for 12 h at the same temperature, the reaction mixture was concentrated in vacuo. The residue was quenched with H2O and then extracted with EtOAc. The combined organic layers were dried over MgSO4 and then concentrated in vacuo. The residue was purified by flash column chromatography on silica gel.
	In tetrahydrofuran; at 20℃; for 3h;	Step 1 : 2-chloro-4-(pyrrolidin-l-yl)pyrimidine <n="88"/>Pyrrolidine (600 μL, 7.31 mmol) and 2,4-dichloropyrimidine (1.0 g, 6.71 mmol) were mixed in THF (20 rnL). The reaction mixture was stirred at RT for 3h then dry loaded on silica gel and purified by flash chromatography (SiO2, gradient eluent 0-50% ethyl acetate in hexanes) to afford 2-chloro-4-(pyrrolidin-l-yl)pyrimidine as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.99 (d, IH), 6.46 (d, IH), 3.43 (t, 2H), 3.32 (t, 2H), 2.0-1.84 (m, 4H). LCMS: 184.1 (M+H)+.

	With triethylamine; In methanol; at 0℃;	General procedure: To a solution of 2,4-dichloropyrimidine and (Et)3N dissolved in methanol was added small molecular anime slowly and stirred for 5 h. The reaction was monitored by TLC until completed. Then the mixture was evaporated, washed with water and filtered to afford a white solid.
	With triethylamine; In dichloromethane; at 20℃; for 4h;	(1) At 0C, add triethylamine (3.84mL) dropwise to 2,4-dichloropyrimidine (2.05g, 13.8mmol) in dichloromethane (30mL) and stir, then add pyrrolidine (0.985g) , 13.8mmol) of dichloromethane (20mL) was added dropwise to the above reaction system, heated to room temperature, reacted for 4h, TLC detection, after the completion of the reaction, washed with saturated brine (30mL×3), and the organic phase was washed with anhydrous MgSO4Dry, filter, concentrate under reduced pressure, and separate and purify by column chromatography (PE:EA=50:1) to obtain 2-chloro-4-(pyrrolidin-1-yl)pyrimidine (compound a)

References: [1]Organic Letters,2018,vol. 20,p. 473 - 476.
[2]Tetrahedron,2015,vol. 71,p. 4859 - 4867.
[3]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 62 - 65.
[4]European Journal of Medicinal Chemistry,1991,vol. 26,p. 729 - 733.
[5]Patent: WO2009/29617,2009,A1 .Location in patent: Page/Page column 86-87.
[6]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29.
[7]European Journal of Medicinal Chemistry,2021,vol. 223.
[8]Patent: CN113307791,2021,A .Location in patent: Paragraph 0044; 0046.

2
[ 288-32-4 ]
[ 35691-20-4 ]
[ 138609-98-0 ]

References: [1]European Journal of Medicinal Chemistry,1991,vol. 26,p. 729 - 733.

3
[ 123-75-1 ]
[ 3934-20-1 ]
[ 35691-20-4 ]
[ 33852-01-6 ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1089 - 1104.
[2]Journal of labelled compounds and radiopharmaceuticals,1998,vol. 41,p. 577 - 584.

4
pyrrolidine-2,2,3,3,4,4,5,5-d<SUB>8 </SUB> [ No CAS ]
[ 35691-20-4 ]
2-[D₈]-pyrrolidinyl-4-pyrrolidinylpyrimidine [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,1998,vol. 41,p. 577 - 584.

5
[ 84713-20-2 ]
[ 35691-20-4 ]
[ 1220596-44-0 ]