872-82-2|2-(1H-Imidazol-5-yl)ethanol| Ambeed

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Quality Control of [ 872-82-2 ] Purity: 95% SDS Specification

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Product Details of [ 872-82-2 ]

CAS No. :	872-82-2
Formula :	C₅H₈N₂O
M.W :	112.13
SMILES Code :	C1=C(CCO)[NH]C=N1
MDL No. :	MFCD00195671
InChI Key :	HEEACTTWORLLPM-UHFFFAOYSA-N
Pubchem ID :	3083655

Safety of [ 872-82-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 872-82-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	5
Fraction Csp3	0.4
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	29.52
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	48.91 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.52
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-0.33
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.06
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.94
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.06

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.66
Solubility	24.7 mg/ml ; 0.22 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.24
Solubility	65.1 mg/ml ; 0.581 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.41
Solubility	4.36 mg/ml ; 0.0389 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.22 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.62

Application In Synthesis of [ 872-82-2 ]

* 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 [ 872-82-2 ]

[ 872-82-2 ] Synthesis Path-Downstream 1~40

1
[ 50-00-0 ]
[ 140-86-3 ]
[ 872-82-2 ]

References: [1]Justus Liebigs Annalen der Chemie,1955,vol. 596,p. 65.
[2]Journal of the Chemical Society. Perkin transactions I,1980,vol. 1,p. 43 - 51.

2
[ 90773-75-4 ]
[ 872-82-2 ]

References: [1]Journal of the Chemical Society,1935,p. 489,491.

3
[ 872-82-2 ]
[ 103-71-9 ]
[ 74294-66-9 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,vol. 1,p. 43 - 51.

4
[ 872-82-2 ]
[ 98-59-9 ]
[ 74294-60-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,vol. 1,p. 43 - 51.

5
[ 55-36-7 ]
[ 872-82-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium nitrite; In water; at 40℃; for 2h;	Dissolve 2 g of histamine hydrochloride in 12 mL of 2 mol/L hydrochloric acid.Stir yellow green solutionWarm up to 40 C.An aqueous solution containing 2.0 g of sodium nitrite was slowly added to the above reaction solution. After the addition, the reaction was continued for 2 h.The solvent was distilled off to give a yellow oily liquid, a small amount of ethanol was added, and the white solid sodium chloride was filtered.The filtrate was spin-dried as crude 4-hydroxyethyl imidazole and used directly in the next reaction.

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,vol. 1,p. 43 - 51.
[2]Patent: CN105367500,2018,B .Location in patent: Paragraph 0107; 0108; 0115; 0122.

6
[ 2637-34-5 ]
[ 872-82-2 ]
2-<<2-<4(5)-imidazolyl>ethyl>thio>pyridine hydrobromide hydrate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3342 - 3350.

Yield	Reaction Conditions	Operation in experiment
		Examples of the imidazole compounds will be given below, which by no means limit them: ... 2-methylimidazole 4-methylimidazole 4-(2-hydroxyethyl)-imidazole 2-ethylimidazole ...

9
4-<β-amino-ethyl>-1(3)<i>H</i>-imidazole hydrochloride [ No CAS ]
[ 872-82-2 ]

References: [1]Chemische Berichte,1911,vol. 44,p. 1724.

10
[ 872-82-2 ]
[ 7732-18-5 ]
[ 645-65-8 ]

References: [1]Pflugers Archiv fur die gesamte Physiologie des Menschen und der Tiere,1931,vol. 228,p. 742,750.

11
[ 50-00-0 ]
[ 140-86-3 ]
[ 7664-41-7 ]
[ 7732-18-5 ]
[ 7758-99-8 ]
[ 872-82-2 ]

References: [1]Justus Liebigs Annalen der Chemie,1955,vol. 596,p. 65.

12
[ 872-82-2 ]
[ 221164-86-9 ]
[ 221167-10-8 ]

Yield	Reaction Conditions	Operation in experiment
28%	With triethylamine; In N,N-dimethyl acetamide; at 120℃; for 15h;	To a solution of the compound in Example 139 (309 mg, 999 mumol) in N,N-dimethylacetamide (10 ml) were added <strong>[872-82-2]4-(2-hydroxyethyl)imidazole</strong> (270 mg, 2.41 mmol) and triethylamine (1 ml) in sequence, and the mixture was stirred for 15 hours at 120 C. The reaction mixture was concentrated under reduced pressure and purified by means of silica gel column chromatography [methylene chloride?methylene chloride-methanol (10:1)] to obtain 114 mg of the title compound as yellowish brown powder. Yield 28%. 1H-NMR(CDCl3,delta):1.47(3H,t,J=6.8 Hz),1.53(3H,t,J=7.3 Hz), 2,81(1H,d,J=4,4 Hz),2.87-2.92(2H,m),3.97(2H,t,J=5.9 Hz), 4.55(2H,q,J=6.8 Hz),4.66(2H,q,J=7.3 Hz),6.94(1H,d,J=1.0 Hz), 7.66(1H,d,J=1.0 Hz),8.15(1H,s),8.42(1H,s).

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 5841 - 5863.
[2]Patent: US6348461,2002,B1 .Location in patent: Page column 137.
[3]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3521 - 3525.

13
[ 24424-99-5 ]
[ 872-82-2 ]
[ 211503-47-8 ]

References: [1]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 881 - 885.

14
[ 872-82-2 ]
[ 908015-61-2 ]

References: [1]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 881 - 885.

15
[ 872-82-2 ]
[ 56-92-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,vol. 1,p. 43 - 51.

16
[ 872-82-2 ]
[ 74294-62-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,vol. 1,p. 43 - 51.

17
[ 2637-34-5 ]
[ 872-82-2 ]
2-[2-(1H-Imidazol-4-yl)ethyl]thio}pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In aqueous HBr;	EXAMPLE 108 2-[2-(1H-Imidazol-4-yl)ethyl]thio}pyridine 0.5 g (4.4 mmol) of 4-(2-hydroxyethyl)-1H-imidazole and 0.49 g (44.4 mmol) of 2-mercaptopyridine are brought to reflux in 5 ml of 47% aqueous HBr for 24 h. The solvent is removed azeotropically with isopropanol under reduced pressure to provide the title compound in the form of a dihydrobromide monohydrate salt which, after crystallization from isopropanol, melts at 189-190 C.

References: [1]Patent: US5559113,1996,A .

18
[ 872-82-2 ]
[ 98-59-9 ]
[ 930768-34-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; dichloromethane; for 0.333333h;	4-lmidazoleacetic acid hydrochloride (5.93 g, 36.47 mmol) in methanol (125 mL) was saturated with HCI gas and stirred at room temperature for 5.5 h, then concentrated to give a quantitative yield of 4-imidazoleacetic acid methyl ester hydrochloride as a white solid which had NMR (MeOH- d4) delta 8.87 (d, J = 1.2 Hz, 1H), 7.46 (s, 1 H), 3.89 (s, 2H) 3.72 <s, 3H). This was added portion-wise to a slurry of lithium aluminum hydride (2.8 g, 74.0 mmol) in THF (150 mL). The mixture, was refluxed for 3h, cooled in ice and carefully quenched with excess sodium sulfate decahydrate. This slurry was dried with anhydrous sodium sulfate and filtered through Celite with ethyl acetate rinse. Concentration gave 2.6 g of a colorless oil that NMR (CDCI3) showed to be a 1.5:1 mixture of starting ester and 2-(1 H-imidazol-4-yl)-ethanol. This crude mixture was slurried in methylene chloride (30 mL) and triethylamine (3.3 mL, 23.6 mmoL) and p-toluenesulfonylchloride (4.45 g, 23.3 mmol) was added. THF (30 mL) was added to help dissolve the starting material. A vigorous reaction ensued. After stirring 20 min, the reaction was concentrated, the residue was partitioned between ethyl acetate and water. The organics were washed with sat. NaHCO3 solution and brine, dried (MgSO4) and concentrated to an oily' white solid. Ether (50 mL) was added and the mixture was stirred vigorously for 30 min. to break up the solid. This material was filtered off and rinsed with ether to give 2.96g (30% from 4-imidazoleacetic acid hydrochloride) of pure 2-[1 -(toluene-4- sulfonyl)-1 H-imidazol-4-yl]-ethanol as a white solid which had: NMR (CDCI3) delta 7.93 (d, J = 1.2Hz, 1H), 7.79 (d, J = 8.3 Hz, 2H), 7.33 (d, J= 8.3 Hz, 2H), 7.05 (d, J = 1.2 Hz, 1 H), 3.83 (t, J = 5.8 Hz, 2H), 2.74-2.71 (m, 2H), 2.42 (s, 3H).

References: [1]Patent: WO2007/34277,2007,A1 .Location in patent: Page/Page column 56.

19
[ 51718-80-0 ]
[ 872-82-2 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h;Heating / reflux;	4-lmidazoleacetic acid hydrochloride (5.93 g, 36.47 mmol) in methanol (125 mL) was saturated with HCI gas and stirred at room temperature for 5.5 h, then concentrated to give a quantitative yield of 4-imidazoleacetic acid methyl ester hydrochloride as a white solid which had NMR (MeOH- d4) delta 8.87 (d, J = 1.2 Hz, 1H), 7.46 (s, 1 H), 3.89 (s, 2H) 3.72 <s, 3H). This was added portion-wise to a slurry of lithium aluminum hydride (2.8 g, 74.0 mmol) in THF (150 mL). The mixture, was refluxed for 3h, cooled in ice and carefully quenched with excess sodium sulfate decahydrate. This slurry was dried with anhydrous sodium sulfate and filtered through Celite with ethyl acetate rinse. Concentration gave 2.6 g of a colorless oil that NMR (CDCI3) showed to be a 1.5:1 mixture of starting ester and 2-(1 H-imidazol-4-yl)-ethanol. This crude mixture was slurried in methylene chloride (30 mL) and triethylamine (3.3 mL, 23.6 mmoL) and p-toluenesulfonylchloride (4.45 g, 23.3 mmol) was added. THF (30 mL) was added to help dissolve the starting material. A vigorous reaction ensued. After stirring 20 min, the reaction was concentrated, the residue was partitioned between ethyl acetate and water. The organics were washed with sat. NaHCO3 solution and brine, dried (MgSO4) and concentrated to an oily' white solid. Ether (50 mL) was added and the mixture was stirred vigorously for 30 min. to break up the solid. This material was filtered off and rinsed with ether to give 2.96g (30% from 4-imidazoleacetic acid hydrochloride) of pure 2-[1 -(toluene-4- sulfonyl)-1 H-imidazol-4-yl]-ethanol as a white solid which had: NMR (CDCI3) delta 7.93 (d, J = 1.2Hz, 1H), 7.79 (d, J = 8.3 Hz, 2H), 7.33 (d, J= 8.3 Hz, 2H), 7.05 (d, J = 1.2 Hz, 1 H), 3.83 (t, J = 5.8 Hz, 2H), 2.74-2.71 (m, 2H), 2.42 (s, 3H).

References: [1]Patent: WO2007/34277,2007,A1 .Location in patent: Page/Page column 56.

20
[ 872-82-2 ]
[ 58479-61-1 ]
[ 1571145-65-7 ]

Yield	Reaction Conditions	Operation in experiment
1.6 g	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 2h;	Preparation 32 4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1H-imidazole A solution of <strong>[872-82-2]2-(1H-imidazol-4-yl)ethanol</strong> (1.24 g, 11.1 mmol) in DMF (10 mL) was treated with imidazole (1.51 g, 22.1 mmol) and TBDPSCl (3.12 mL, 12.2 mmol) and the mixture was stirred at RT for 2 h. The mixture was then poured onto H2O and extracted with AcOEt. The combined org. layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, AcOEt/heptane 0:100 to 100:0) gave the title compound (1.6 g). UPLC-MS: MS 351.2 (M+H+); UPLC rt 1.02 min.
1.6 g	With 1H-imidazole; at 20℃; for 2h;	A solution of 2-(1 H-imidazoM-yl)ethanol (1.24 g, 11.1 mmol) in DMF (10 mL) was treated with imidazole (1.51 g, 22.1 mmol) and TBDPSCI (3.12 mL, 12.2 mmol) and the mixture was stirred at RT for 2h. The mixture was then poured onto H20 and extracted with AcOEt. The combined org. layers were dried over Na2S04, filtered and concentrated in vacuo. Purification by flash chromatography (Si02, AcOEt heptane 0:100 to 100:0) gave the title compound (1.6 g). UPLC-MS: MS 351.2 (M+H+); UPLC rt 1.02 min.

References: [1]Patent: US2014/57902,2014,A1 .Location in patent: Paragraph 0785-0786.
[2]Patent: WO2014/30128,2014,A1 .Location in patent: Page/Page column 87; 88.

21
[ 872-82-2 ]
tert-butyl 2-chloro-4-iodobenzoate [ No CAS ]
tert-butyl 2-chloro-4-(4-(2-hydroxyethyl)-1H-imidazol-1-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; potassium phosphate; copper(l) iodide; In dimethyl sulfoxide; at 20 - 50℃; for 2h;Inert atmosphere;	To a suspension of tert-butyl 2-chloro-4-iodobenzoate (0.44 mmol, 150 mg), copper(I) iodide (0.44 mmol, 84 mg), 2-(lH-imidazol-4-yl)ethanol (0.44 mmol, 50 mg) and tripotassium phosphate (1.33 mmol, 282 mg) in DMSO (2 mL) was added (0936) trans-N,N'-dimethylcyclohexane-l,2-diamine (0.89 mmol, 126 mg) at RT and it was degassed under nitrogen atmosphere. The mixture was stirred at 50 C for 2 h. The reaction mixture was quenched with water and extracted with EtOAc, washed with water (2 times), and concentrated in vacuo. Purification by column chromatography on silica gel (5% MeOH in EtOAc) gave the title compound. (0937) 1H NMR (300 MHz, CDC13) delta (ppm): 7.88 (1H, d, J= 8.2 Hz), 7.83 (1H, d, J= 1.4 Hz), 7.46 (1H, d, J= 2.4 Hz), 7.31 (1H, dd, J= 8.4, 2.2 Hz), 7.12 (1H, t, J= 0.7 Hz), 3.95 (2H, t, J= 5.7 Hz), 2.87 (2H, t, J= 5.3 Hz), 1.63 (9H, d, J= 2.7 Hz)

References: [1]Patent: WO2015/160634,2015,A1 .Location in patent: Page/Page column 125.

22
[ 872-82-2 ]
[ 76-83-5 ]
[ 127607-62-9 ]

Yield	Reaction Conditions	Operation in experiment
40%	With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 12h;	Triphenylmethyl chloride (29.84 g, 107.0 mmol, 1.2 eq) is added at room temperature to a stirred solution of <strong>[872-82-2]2-(1H-imidazol-4-yl)ethanol</strong> (10.0 g, 89.18 mmol, 1.0 eq) [872-82-2] in N,N-dimethylformamide (300 mL), followed by triethylamine (14.92 mL, 107.0 mmol, 1.2 eq). After 12 hours stirring at room temperature, the reaction mixture is poured into crushed ice and the resulting solid is collected by filtration, washed with water and acetone to afford 2-(1-tritylimidazol-4-yl)ethanol as a white solid (12.5 g, 40% yield). 1H-NMR (400 MHz, DMSO-d6) ^ ppm: 7.38 (m, 9H), 7.24 (s, 1H), 7.08 (m, 6H), 6.65 (s, 1H), 4.52 (t, J = 5.6 Hz, 1H), 3.57 (m, 2H), 2.58 (t, J = 7.2 Hz, 2H). MS m/z (+ESI): 355.2 [M+H]+

References: [1]Patent: WO2016/198691,2016,A1 .Location in patent: Page/Page column 201.

23
[ 872-82-2 ]
[ 76-83-5 ]
methyl 4-nitro-3-[2-(1-tritylimidazol-4-yl)ethoxy]benzoate [ No CAS ]

References: [1]Patent: WO2016/198691,2016,A1 .

24
[ 5305-59-9 ]
[ 872-82-2 ]
2-(1-(6-aminopyrimidin-4-yl)-1H-imidazole-4-yl)ethan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With caesium carbonate; In N,N-dimethyl-formamide; at 140℃; for 12h;	A solution of 1.12 g (10 mmol) of 2- (1 H-imidazol-4-yl) ethan-1-ol was dissolved in 20 ml of DMF, 1.30 g of (lOmmol) of 4-amino-6-chloroetine, g (12 mmol) of cesium carbonate, the temperature was raised to 140 C and the reaction was stirred for 12 h. And the residue was purified by silica gel column chromatography. The eluent was methanol: dichloromethane = 1: 30 to give 1.19 g of the compound as shown on the white solid (yield of the compound of the formula IIb-1) in a yield of 58%.
58%	With caesium carbonate; In N,N-dimethyl-formamide; at 140℃; for 12h;	General procedure: A mixture of imidazole derivatives (4a-c, 10mmol), 4-amino-6-chloropyrimidine (1.30g, 10mmol), and K2CO3 (2.07g, 15mmol, for 5a) or Cs2CO3 (3.91g, 12mmol, for 5b-c) was stirred in DMF (20mL) at 100C (for 5a) or at 140C (for 5b-c) for 12h. Water (100mL) was then added. The mixture was extracted with EtOAc (3×50mL). The organic layer was separated and dried over Na2SO4. Removal of the solvents produced a residue which was purified using column chromatography and eluted with a mixture of MeOH:CH2Cl2 (1:30, v:v) to afford 5a-c.

References: [1]Patent: CN106946854,2017,A .Location in patent: Paragraph 0047; 0048; 0049; 0050.
[2]European Journal of Medicinal Chemistry,2018,vol. 143,p. 33 - 47.

25
[ 872-82-2 ]
tert-butyl 2-chloro-4-iodobenzoate [ No CAS ]
C₁₁H₁₀ClN₃O₃*(x)ClH [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2622 - 2628.

26
[ 872-82-2 ]
1-(6-(4-(2-bromoethyl)-1H-imidazol-1-yl)pyrimidin-4-yl)-3-ethylthiourea [ No CAS ]