[ CAS No. 192197-34-5 ] {[proInfo.proName]}

Name: 192197-34-5|2-(Pyrrolidin-1-yl)pyrimidine|97%
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SKU: A231947
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Quality Control of [ 192197-34-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 192197-34-5 ]

Product Details of [ 192197-34-5 ]

CAS No. :	192197-34-5	MDL No. :	MFCD28161447
Formula :	C₈H₁₁N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PCXCZMYBFGWKKH-UHFFFAOYSA-N
M.W :	149.19	Pubchem ID :	12099397
Synonyms :

Calculated chemistry of [ 192197-34-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.67
TPSA :	29.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	1.15
Log Po/w (WLOGP) :	0.7
Log Po/w (MLOGP) :	0.75
Log Po/w (SILICOS-IT) :	1.37
Consensus Log Po/w :	1.18

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.83
Solubility :	2.22 mg/ml ; 0.0149 mol/l
Class :	Very soluble
Log S (Ali) :	-1.35
Solubility :	6.6 mg/ml ; 0.0443 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.08
Solubility :	1.25 mg/ml ; 0.00836 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 192197-34-5 ]

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

Application In Synthesis of [ 192197-34-5 ]

* 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.

Upstream synthesis route of [ 192197-34-5 ]
Downstream synthetic route of [ 192197-34-5 ]

[ 192197-34-5 ] Synthesis Path-Upstream 1~2

1
[ 123-75-1 ]
[ 1722-12-9 ]
[ 192197-34-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1-methyl-3-(2-pyridinyl)-3,4,5,6-tetrahydropyrimidin-3-ium hexafluorophosphate; potassium <i>tert</i>-butylate; palladium diacetate In 1,2-dimethoxyethane at 100℃; for 0.666667 h; Microwave irradiation	General procedure: The Buchwald–Hartwig amination reaction under microwave irradiation was conducted in a CEM Discover apparatus. A 10-mL Teflon vessel was charged with 1.0 mmol of hetero-aryl halide, 3.0 mmol of amine, 2.0 of mmol base, 0.05 mmol of Pd(OAc)₂ , 0.10 mmol of LHX, and 2.0 mL of solvent. The mixture was irradiated at 150 W at 100 °C for the specified time and then allowed to cool. The reaction mixture was extracted 3 times with diethyl ether, and the combined organic extracts were washed with water, dried (MgSO₄) , and evaporated to dryness. Purification of the residue by flash chromatography on silica gel afforded the pure products.
76%	Stage #1: With sodium hydride In tetrahydrofuran; mineral oil for 0.5 h; Reflux Stage #2: for 48 h; Reflux	Example 5 Synthesis of HK-9, HK-11, HK-13 and HK-15 The following describes the general synthesis of 2-(pyrrolidine-1-yl)pyrimidine (HK-9), 4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine, HK-11, 2-(piperidine-1-yl)pyrimidine (HK-13), 4,6-dimethoxy-2-(piperidine-1-yl)pyrimidine (HK-15), 5-benzyloxy-2-(pyrrolidine-1-yl)pyrimidine (Compound 35), 5-benzyloxy-2-(piperidine-1-yl)pyrimidine (Compound 36), 5-benzyloxy-4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine (Compound 37), and 5-benzyloxy-4,6-dimethoxy-2-(piperidine-1-yl)pyrimidine (Compound 38). Referring to the reaction scheme of , to 9.53 mL (116 mmol) pyrrolidine (29) in 400 mL of anhydrous THF was added 2.78 g of sodium hydride (116 mmol) and the mixture was refluxed for 0.5 hr. After cooling to r.t., 12 g (105 mmol) of 2-chloropyrimidine (33) was added dropwise and the mixture was refluxed for 2 days and then cooled in an ice bath. Water (200 mL) was then added to the cooled reaction mixture and the THF was removed in vacuo. The aqueous residue was extracted with CHCl₃ and the combined CHCl₃ extracts were washed with brine, dried over magnesium sulfate, and filtered. After removal of solvent in vacuo, the residue was purified by silica gel column chromatography using 20:1 hexanes:EtOAc as eluent. The product was then recrystallized from diethyl ether (Et₂O) to give a 12.0 g (76percent) of HK-9 as a yellow solid, mp 39.0-39.6° C. ¹H NMR (CDCl₃) δ 8.31 (d, J=4.88 Hz, 2H), 6.45 (t, J=4.88 Hz, 1H), 3.57 (t, J=4.4 Hz, 4H), 2.01-1.98 (m, 4H). Anal. Calcd for C₈H₁₁N₃; C, 64.40; H, 7.43; N, 28.16. Found: C, 64.42; H, 7.53; N, 27.97.

Reference： [1] Turkish Journal of Chemistry, 2015, vol. 39, # 1, p. 121 - 129
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 36, p. 5957 - 5963
[3] Tetrahedron Letters, 2004, vol. 45, # 4, p. 757 - 759
[4] ChemSusChem, 2013, vol. 6, # 8, p. 1455 - 1460
[5] Patent: US2014/235858, 2014, A1, . Location in patent: Paragraph 0077
[6] Journal of Medicinal Chemistry, 2015, vol. 58, # 22, p. 8796 - 8805
[7] Pesticide Science, 1997, vol. 50, # 3, p. 258 - 274
[8] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 3, p. 343 - 348

2
[ 123-75-1 ]
[ 4595-60-2 ]
[ 192197-34-5 ]

Reference： [1] ChemSusChem, 2013, vol. 6, # 8, p. 1455 - 1460

[ 192197-34-5 ] Synthesis Path-Downstream 1~10

1
[ 123-75-1 ]
[ 1722-12-9 ]
[ 192197-34-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium phosphate; benzoin oxime; copper diacetate; In dimethyl sulfoxide; at 80.0℃;Inert atmosphere;	General procedure: K3PO4 (5.62 mmol) in DMSO (4 mL), were added Cu(OAc)2 (0.28 mmol). The flask was evacuatedand backfilled with argon for three times. The resulting suspension was heated in a 80 C oil bathwith stirring for the indicated time. The reactor was cooled to r.t., the flask was opened to air and thereaction mixture was poured into water (20 mL), extracted with ethyl acetate (20 mL × 3), andorganic layer was washed with water (20 mL × 2) and once with brine (25 mL), dried overmagnesium sulfate and concentrated in vacuo. The product was purified by column chromatographyon silica gel using petroleum ether and ethyl acetate as eluent.1-(2-Methoxyphenyl)-1H-pyrrole (3a) [30]: colorless oil (0.43 g, 88%). 1H-NMR (400 MHz, CDCl3) delta (ppm):7.30-7.23 (2H, m), 7.03-6.98 (4H, m), 6.30 (2H,
87%	With 1-methyl-3-(2-pyridinyl)-3,4,5,6-tetrahydropyrimidin-3-ium hexafluorophosphate; potassium tert-butylate; palladium diacetate; In 1,2-dimethoxyethane; at 100.0℃; for 0.666667h;Microwave irradiation;	General procedure: The Buchwald-Hartwig amination reaction under microwave irradiation was conducted in a CEM Discover apparatus. A 10-mL Teflon vessel was charged with 1.0 mmol of hetero-aryl halide, 3.0 mmol of amine, 2.0 of mmol base, 0.05 mmol of Pd(OAc)2 , 0.10 mmol of LHX, and 2.0 mL of solvent. The mixture was irradiated at 150 W at 100 C for the specified time and then allowed to cool. The reaction mixture was extracted 3 times with diethyl ether, and the combined organic extracts were washed with water, dried (MgSO4) , and evaporated to dryness. Purification of the residue by flash chromatography on silica gel afforded the pure products.
76%		Example 5 Synthesis of HK-9, HK-11, HK-13 and HK-15 The following describes the general synthesis of 2-(pyrrolidine-1-yl)pyrimidine (HK-9), 4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine, HK-11, 2-(piperidine-1-yl)pyrimidine (HK-13), 4,6-dimethoxy-2-(piperidine-1-yl)pyrimidine (HK-15), 5-benzyloxy-2-(pyrrolidine-1-yl)pyrimidine (Compound 35), 5-benzyloxy-2-(piperidine-1-yl)pyrimidine (Compound 36), 5-benzyloxy-4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine (Compound 37), and 5-benzyloxy-4,6-dimethoxy-2-(piperidine-1-yl)pyrimidine (Compound 38). Referring to the reaction scheme of , to 9.53 mL (116 mmol) pyrrolidine (29) in 400 mL of anhydrous THF was added 2.78 g of sodium hydride (116 mmol) and the mixture was refluxed for 0.5 hr. After cooling to r.t., 12 g (105 mmol) of 2-chloropyrimidine (33) was added dropwise and the mixture was refluxed for 2 days and then cooled in an ice bath. Water (200 mL) was then added to the cooled reaction mixture and the THF was removed in vacuo. The aqueous residue was extracted with CHCl3 and the combined CHCl3 extracts were washed with brine, dried over magnesium sulfate, and filtered. After removal of solvent in vacuo, the residue was purified by silica gel column chromatography using 20:1 hexanes:EtOAc as eluent. The product was then recrystallized from diethyl ether (Et2O) to give a 12.0 g (76%) of HK-9 as a yellow solid, mp 39.0-39.6 C. 1H NMR (CDCl3) delta 8.31 (d, J=4.88 Hz, 2H), 6.45 (t, J=4.88 Hz, 1H), 3.57 (t, J=4.4 Hz, 4H), 2.01-1.98 (m, 4H). Anal. Calcd for C8H11N3; C, 64.40; H, 7.43; N, 28.16. Found: C, 64.42; H, 7.53; N, 27.97.

Reference： [1]Molecules,2019,vol. 24
[2]Turkish Journal of Chemistry,2015,vol. 39,p. 121 - 129
[3]European Journal of Organic Chemistry,2016,vol. 2016,p. 5957 - 5963
[4]Tetrahedron Letters,2004,vol. 45,p. 757 - 759
[5]ChemSusChem,2013,vol. 6,p. 1455 - 1460
[6]Patent: US2014/235858,2014,A1 .Location in patent: Paragraph 0077
[7]Journal of Medicinal Chemistry,2015,vol. 58,p. 8796 - 8805
[8]Journal of Organic Chemistry,2019,vol. 84,p. 15343 - 15354
[9]Pesticide Science,1997,vol. 50,p. 258 - 274
[10]Journal of Heterocyclic Chemistry,2004,vol. 41,p. 343 - 348

2
[ 64-19-7 ]
[ 192197-34-5 ]
1-(Hexahydropyrimidin-2-yl)pyrrolidinium acetate [ No CAS ]

Reference： [1]Pesticide Science,1997,vol. 50,p. 258 - 274

3
[ 74-85-1 ]
[ 192197-34-5 ]
2,5-diethyl-1-(2-pyrimidinyl)pyrrolidine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 10935 - 10941

4
2-pyrrol-1-yl-pyrimidine [ No CAS ]
[ 192197-34-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,2004,vol. 41,p. 343 - 348

5
[ 123-75-1 ]
[ 4595-60-2 ]
[ 192197-34-5 ]

Reference： [1]ChemSusChem,2013,vol. 6,p. 1455 - 1460

Yield	Reaction Conditions	Operation in experiment
90%	With (5,5-dimethyl-1,3-dipicolyl-3,4,5,6-tetrahydropyrimidin-2-ylidenes)PdCl*PF6; potassium tert-butylate; at 100.0℃; for 0.5h;Microwave irradiation;	General procedure: Partial C-N Coupled Catalytic Reaction Examples:Halogenated aromatic hydrocarbons (1.0 mmol),Amine (3.0 mmol), base (2.0 mmol),The pared expandable nitrogen heterocyclic carbene palladium compound catalyst (0.01 mmol) of the invention is added to a solvent, and after being reacted under the microwave radiation for 50 to 100 DEG C for 10 to 40 minutes,Drop to room temperature,The solvent was removed under reduced pressure,Column chromatography to obtain pure product.

7
[ 78-94-4 ]
[ 192197-34-5 ]
4-(1-(pyrimidin-2-yl)pyrrolidin-2-yl)butan-2-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 9056 - 9060

8
[ 123-75-1 ]
[ 14080-23-0 ]
[ 192197-34-5 ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 7142 - 7150

9
[ 73183-34-3 ]
[ 192197-34-5 ]
[ 1015242-07-5 ]

Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 3596 - 3604

10
[ 192197-34-5 ]
5-(difluoromethyl)-2-(pyrrolidin-1-yl)pyrimidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 3596 - 3604

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H226	Flammable liquid and vapour
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
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H250	Catches fire spontaneously if exposed to air
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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Health hazards
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H301	Toxic if swallowed
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H315	Causes skin irritation
H316	Causes mild skin irritation
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H318	Causes serious eye damage
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H320	Causes eye irritation
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H333	May be harmful if inhaled
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 192197-34-5 ] {[proInfo.proName]}

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[ 192197-34-5 ] Synthesis Path-Downstream 1~10

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Pyrrolidines

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