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[ CAS No. 257280-25-4 ] {[proInfo.proName]}

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Chemical Structure| 257280-25-4

Chemical Structure| 257280-25-4

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Quality Control of [ 257280-25-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 257280-25-4 ]

CAS No. :	257280-25-4	MDL No. :	MFCD03646346
Formula :	C₁₀H₇BrN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZFECRMYYOMVREH-UHFFFAOYSA-N
M.W :	251.08	Pubchem ID :	642842
Synonyms :

Calculated chemistry of [ 257280-25-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	56.25
TPSA :	35.01 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.44
Log Po/w (XLOGP3) :	2.76
Log Po/w (WLOGP) :	3.03
Log Po/w (MLOGP) :	2.08
Log Po/w (SILICOS-IT) :	2.66
Consensus Log Po/w :	2.6

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.64
Solubility :	0.0578 mg/ml ; 0.00023 mol/l
Class :	Soluble
Log S (Ali) :	-3.15
Solubility :	0.178 mg/ml ; 0.000707 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.77
Solubility :	0.00429 mg/ml ; 0.0000171 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.98

Safety of [ 257280-25-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 257280-25-4 ]

* 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.

Upstream synthesis route of [ 257280-25-4 ]
Downstream synthetic route of [ 257280-25-4 ]

[ 257280-25-4 ] Synthesis Path-Upstream 1~5

1
[ 183438-24-6 ]
[ 108-95-2 ]
[ 257280-25-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	at 165℃; for 4 h; Inert atmosphere	Step A: Preparation of 5-bromo-2-phenoxypyrimidine A mixture consisting of 5-bromo-2-iodopyrimidine (Bridge Organics, 1.01 g, 3.57 mmol), phenol (Aldrich, 3.35 g, 35.7 mmol), and potassium carbonate (Aldrich, 4.93 g, 35.7 mmol) was stirred neat at 165° C. under a nitrogen atmosphere for four hours. After cooling to room temperature, the mixture was partitioned between ethyl acetate (250 mL) and 1 N hydrochloric acid (4*200 mL). The organic layer was washed with 1 N hydrochloric acid until disappearance of color in the aqueous layer. The phases were separated and the organic phase was washed with water (100 mL) and brine (100 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide an orange oil (1.1 g). The product was purified by flash silica column chromatography. Elution through an 80-g Silicycle.(R). flash silica cartridge with 10percent ethyl acetate in hexanes afforded the title compound as a white solid (0.82 g, 92percent yield); R_f 0.51 with 8:2 v/v hexanes-ethyl acetate; ¹H-NMR (400 MHz; CDCl₃) δ 8.56 (s, 2H), 7.46-7.41 (m, 2H), 7.30-7.24 (m, 1H), 7.20-7.16 (m, 2H); MS (APCI⁺) m/z 252.9 (M+1).
87%	With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 100℃; for 20 h; Inert atmosphere	Procedure: 5-bromo-2-iodopyrimidine (3 mmol), phenol (3.2 mmol), 2-picolinic acid (0.3 mmol), cuprous iodide CuI (0.3 mmol), potassium phosphate (4.5 mmol) was placed in 25 mL dry In a flask, 15 mL of DMSO was added and the mixture was heated to 100° C. under Ar protection. After about 20 hours of reaction, TLC conversion was complete. After the mixture was cooled to room temperature, a large amount of ethyl acetate was added, washed with water four times and extracted twice with ethyl acetate. The EA phases were combined and washed with saturated brine. The organic phase was dried, filtered, evaporated to dryness and purified by silica gel column chromatography to give 1.1 g of a white product. , Yield 87percent

Reference： [1] Patent: US2010/75990, 2010, A1, . Location in patent: Page/Page column 40
[2] Patent: CN108069974, 2018, A, . Location in patent: Paragraph 0194-0196

2
[ 98-80-6 ]
[ 257280-25-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With oxygen; caesium carbonate In 1,2-dimethoxyethane at 20℃; for 10 h;	Example 40 5-Bromo-2-phenoxypyrimidine 3-(5-Bromo-pyrimidin-2-yloxy)-3H-[1,2,3]triazolo[4,5-b]pyridine (100 mg, 0.34 mmole) was dissolved in DME (4 mL) at RT and phenyl boronic acid (125 mg, 1.02 mmole) was added to it. Cs₂CO₃ (443 mg, 1.36 mmole) and Pd(PPh₃)₄ (39 mg, 0.03 mmole) was added to the reaction mixture and purged with O₂. The reaction mixture was then stirred at RT for 10 h and was directly purified by flash chromatography to afford a white solid (60 mg, 70percent). ¹H-NMR (CDCl₃, 300 MHz) δ (ppm) 8.57 (s, 2H), 7.44 (m, 2H), 7.26 (m, 1H), 7.17 (d, 2H, J=4.2 Hz). LCMS (ES-MS) [(M+H)+]: for C₁₀H₇BrN₂O 251.07, found 251.30.

Reference： [1] Patent: US2009/291971, 2009, A1, . Location in patent: Page/Page column 28
[2] Organic Letters, 2009, vol. 11, # 12, p. 2511 - 2514
[3] Tetrahedron Letters, 2009, vol. 50, # 41, p. 5733 - 5736

3
[ 32779-36-5 ]
[ 108-95-2 ]
[ 257280-25-4 ]

Reference： [1] Patent: US2002/156081, 2002, A1,
[2] Patent: US6921763, 2005, B2,

4
[ 38353-06-9 ]
[ 257280-25-4 ]

Reference： [1] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 22, p. 3265 - 3268

5
[ 66003-76-7 ]
[ 38353-06-9 ]
[ 257280-25-4 ]

Reference： [1] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 22, p. 3265 - 3268

[ 257280-25-4 ] Synthesis Path-Downstream 1~15

1
diphenyliodonium tetrafluoroborate [ No CAS ]
[ 38353-06-9 ]
[ 257280-25-4 ]
5-Bromo-1-phenylpyrimidin-2(1H)-one [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 3265 - 3268

2
[ 66003-76-7 ]
[ 38353-06-9 ]
[ 257280-25-4 ]
5-Bromo-1-phenylpyrimidin-2(1H)-one [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 3265 - 3268

3
[ 73183-34-3 ]
[ 257280-25-4 ]
[ 330792-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate; In n-heptane; dichloromethane; N,N-dimethyl-formamide;	2-Phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyrimidine (intermediate AV) A mixture of 5-bromo-2-phenoxy-pyrimidine (intermediate AU) (3.00 g, 0.0119 mol), diboron pinacol ester (3.64 g, 0.0143 mol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (0.29 g, 0.00036 mol) and potassium acetate (3.52 g, 0.0358 mol) in N,N-dimethylformamide (70 ml) was heated at 80 C. under a nitrogen atmosphere overnight. The mixture was allowed to cool to ambient temperature and then most of the solvent was removed under reduced pressure. Dichloromethane (70 ml) was added to the residue and the resulting solids were removed by filtration through a pad of celite. The filtrate was concentrated to leave dark oil. The residue was dissolved in dichloromethane (5 mL) and added to heptane (75 mL). The mixture was filtered, and the precipitate was slurried in heptane (75 mL) for 17 hours. After filtration and drying and dried in vacuo 2-phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrimidine was obtained as a grey solid (2.95 g, 0.00989 mol): 1H NMR (DMSO-d6, 400 MHz) 8.75 (s, 2H), 7.45 (t, 2H), 7.27 (t, 1H), 7.20 (d, 2H), 1.31 (s, 12H) Cis-1-[4-(4-methylpiperazino)cyclohexyl]-3-(2-phenoxy-5-pyrimidinyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. (intermediate AW)
	With potassium acetate; In n-heptane; dichloromethane; N,N-dimethyl-formamide;	2-Phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyrimidine (intermediate AV) A mixture of 5-bromo-2-phenoxy-pyrimidine (intermediate AU) (3.00 g, 0.0119 mol), diboron pinacol ester (3.64 g, 0.0143 mol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (0.29 g, 0.00036 mol) and potassium acetate (3.52 g, 0.0358 mol) in N,N-dimethylformamide (70 ml) was heated at 80 C. under a nitrogen atmosphere overnight. The mixture was allowed to cool to ambient temperature and then most of the solvent was removed under reduced pressure. Dichloromethane (70 ml) was added to the residue and the resulting solids were removed by filtration through a pad of celite. The filtrate was concentrated to leave dark oil. The residue was dissolved in dichloromethane (5 mL) and added to heptane (75 mL). The mixture was filtered, and the precipitate was slurried in heptane (75 mL) for 17 hours. After filtration and drying and dried in vacuo 2-phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrimidine was obtained as a grey solid (2.95 g, 0.00989 mol): 1H NMR (DMSO-d6, 400 MHz) 8.75 (s, 2H), 7.45 (t, 2H), 7.27 (t, 1H), 7.20 (d, 2H), 1.31 (s, 12H)

Reference： [1]Patent: US2002/156081,2002,A1
[2]Patent: US6921763,2005,B2

4
[ 32779-36-5 ]
[ 108-95-2 ]
[ 257280-25-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In n-heptane; ethyl acetate; toluene;	5-Bromo-2-phenoxypyrimidine (intermediate AU) A mixture of 5-bromo-2-chloropyrimidine (5.00 g, 0.0259 mol), phenol (3.16 g, 0.0336 mol), dibenzo-18-crown-6 (0.47 g, 0.0013mol) and ground potassium hydroxide (3.51 g, 0.0626 mol) in toluene (75 ml) was heated at reflux for 5 hours with azeotropic removal of water. The mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure. The residue was partitioned between water and chloroform. The layers were separated and the aqueous phase was extracted with chloroform three times. The combined organic layers were dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography on silica using n-heptane/ethyl acetate (98:2) as an eluent to give 5-bromo-2-phenoxy-pyrimidine as a white solid (3.55 g, 0.0141 mol): 1H NMR (DMSO-d6, 400 MHz) 8.80 (s, 2H), 7.45 (t, 2H), 7.27 (t, 1H), 7.22 (d 2H); TLC (n-heptane/ethyl acetate=95:5) Rf 0.20
	With potassium hydroxide; In n-heptane; ethyl acetate; toluene;	5-Bromo-2-phenoxypyrimidine (intermediate AU) A mixture of 5-bromo-2-chloropyrimidine (5.00 g, 0.0259 mol), phenol (3.16 g, 0.0336 mol), dibenzo-18-Crown-6 (0.47 g, 0.0013 mol) and ground potassium hydroxide (3.51 g, 0.0626 mol) in toluene (75 ml) was heated at reflux for 5 hours with azeotropic removal of water. The mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure. The residue was partitioned between water and chloroform. The layers were separated and the aqueous phase was extracted with chloroform three times. The combined organic layers were dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography on silica using n-heptane/ethyl acetate (98:2) as an eluent to give 5-bromo-2-phenoxy-pyrimidine as a white solid (3.55 g, 0.0141 mol): 1H NMR (DMSO-d6, 400 MHz) 8.80 (s, 2H), 7.45 (t, 2H), 7.27 (t, 1H), 7.22 (d 2H); TLC (n-heptane/ethyl acetate=95:5) Rf 0.20.

Reference： [1]Patent: US2002/156081,2002,A1
[2]Patent: US6921763,2005,B2

5
3-(5-bromo-pyrimidin-2-yloxy)-3H-[1,2,3]triazolo[4,5-b]pyridine [ No CAS ]
[ 98-80-6 ]
[ 257280-25-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With oxygen; caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 20℃; for 10h;Product distribution / selectivity;	Example 40 5-Bromo-2-phenoxypyrimidine 3-(5-Bromo-pyrimidin-2-yloxy)-3H-[1,2,3]triazolo[4,5-b]pyridine (100 mg, 0.34 mmole) was dissolved in DME (4 mL) at RT and phenyl boronic acid (125 mg, 1.02 mmole) was added to it. Cs2CO3 (443 mg, 1.36 mmole) and Pd(PPh3)4 (39 mg, 0.03 mmole) was added to the reaction mixture and purged with O2. The reaction mixture was then stirred at RT for 10 h and was directly purified by flash chromatography to afford a white solid (60 mg, 70%). 1H-NMR (CDCl3, 300 MHz) delta (ppm) 8.57 (s, 2H), 7.44 (m, 2H), 7.26 (m, 1H), 7.17 (d, 2H, J=4.2 Hz). LCMS (ES-MS) [(M+H)+]: for C10H7BrN2O 251.07, found 251.30.

Reference： [1]Patent: US2009/291971,2009,A1 .Location in patent: Page/Page column 28
[2]Organic Letters,2009,vol. 11,p. 2511 - 2514
[3]Tetrahedron Letters,2009,vol. 50,p. 5733 - 5736

6
[ 183438-24-6 ]
[ 108-95-2 ]
[ 257280-25-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; at 165℃; for 4h;Inert atmosphere;	Step A: Preparation of 5-bromo-2-phenoxypyrimidine A mixture consisting of 5-bromo-2-iodopyrimidine (Bridge Organics, 1.01 g, 3.57 mmol), phenol (Aldrich, 3.35 g, 35.7 mmol), and potassium carbonate (Aldrich, 4.93 g, 35.7 mmol) was stirred neat at 165 C. under a nitrogen atmosphere for four hours. After cooling to room temperature, the mixture was partitioned between ethyl acetate (250 mL) and 1 N hydrochloric acid (4*200 mL). The organic layer was washed with 1 N hydrochloric acid until disappearance of color in the aqueous layer. The phases were separated and the organic phase was washed with water (100 mL) and brine (100 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide an orange oil (1.1 g). The product was purified by flash silica column chromatography. Elution through an 80-g Silicycle flash silica cartridge with 10% ethyl acetate in hexanes afforded the title compound as a white solid (0.82 g, 92% yield); Rf 0.51 with 8:2 v/v hexanes-ethyl acetate; 1H-NMR (400 MHz; CDCl3) delta 8.56 (s, 2H), 7.46-7.41 (m, 2H), 7.30-7.24 (m, 1H), 7.20-7.16 (m, 2H); MS (APCI+) m/z 252.9 (M+1).
87%	With 2-Picolinic acid; potassium phosphate; copper(l) iodide; In dimethyl sulfoxide; at 100℃; for 20h;Inert atmosphere;	Procedure: 5-bromo-2-iodopyrimidine (3 mmol), phenol (3.2 mmol), 2-picolinic acid (0.3 mmol), cuprous iodide CuI (0.3 mmol), potassium phosphate (4.5 mmol) was placed in 25 mL dry In a flask, 15 mL of DMSO was added and the mixture was heated to 100 C. under Ar protection. After about 20 hours of reaction, TLC conversion was complete. After the mixture was cooled to room temperature, a large amount of ethyl acetate was added, washed with water four times and extracted twice with ethyl acetate. The EA phases were combined and washed with saturated brine. The organic phase was dried, filtered, evaporated to dryness and purified by silica gel column chromatography to give 1.1 g of a white product. , Yield 87%
87%	With copper(l) iodide; In dimethyl sulfoxide; at 100℃; for 20h;Inert atmosphere;	5-bromo-2-iodopyrimidine (3mmol), phenol (3.2mmol), 2-picolinic acid (0.3mmol), cuprous iodide CuI (0.3mmol), potassium phosphate (4.5mmol) was dried in 25mL In the passed flask, 15 mL of DMSO was added, and heated to 100 degrees under the protection of Ar. The reaction was carried out for about 20 hours, and the TLC conversion was complete. Reduce to room temperature, add a large amount of ethyl acetate, wash 4 times with water, extract 2 times with ethyl acetate, combine EA phases, wash with saturated brine, dry the organic phase, filter, spin dry, and purify by silica gel column chromatography to obtain 1.1 g of white product The yield is 87%.

	With potassium carbonate; In dimethyl sulfoxide; at 120℃; for 1h;	5-bromo-2-iodopyrimidine (Formula 4-1, 0.5 g, 1.76 mmol) was dissolved in DMSO (25 ml), followed by phenol (Formula 12-1, 0.232 ml, 2.63 mmol, 1.5 eq) and K 2 CO 3 (485 mg, 3.51 mmol, 2 eq) was added dropwise at room temperature. The reaction mixture was stirred at 120 C. for 1 hour and then cooled to room temperature. The reaction of the reaction mixture was terminated with H 2 O and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO 4, and the organic layer was decompressed to remove the solvent. Thereafter, the reaction mixture was separated and purified by MPLC (hexane / ethyl acetate; 90:10) to obtain a target compound (Formula 12-2).
	With potassium carbonate; In dimethyl sulfoxide; at 120℃; for 1h;	5-Bromo-2-iodopyrimidine (Formula 4-1, 0.5 g, 1.76 mmol) was dissolved in DMSO (25 ml), followed by phenol (Formula 12-1, 0.232 ml, 2.63 mmol, 1.5 eq) and K2CO3 (485 mg, 3.51 mmol, 2 eq) was added dropwise at room temperature. The reaction mixture was stirred at 120 C. for 1 hour and then cooled to room temperature. The reaction of the reaction mixture was terminated with H2O and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4, and the organic layer was reduced in pressure to remove the solvent. Then, the reaction mixture was separated and purified by MPLC (hexane / ethyl acetate; 90:10) to obtain the target compound (Formula 12-2).

Reference： [1]Patent: US2010/75990,2010,A1 .Location in patent: Page/Page column 40
[2]Patent: CN108069974,2018,A .Location in patent: Paragraph 0194-0196
[3]Patent: CN110483521,2019,A .Location in patent: Paragraph 0149-0151
[4]Patent: KR2019/109007,2019,A .Location in patent: Paragraph 0263-0266
[5]Patent: KR2020/30970,2020,A .Location in patent: Paragraph 0377-0380

7
[ 661-69-8 ]
[ 257280-25-4 ]
[ 1254171-30-6 ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 80℃; for 12h;Inert atmosphere;	Synthesis of 2-(2-chloro-6-fluorophenyl)-5-(2-phenoxypyrimidin-5-yl)- lH-imidazole-4-carbonitrile (EX-43)[000265] A solution of <strong>[257280-25-4]5-bromo-2-phenoxypyrimidine</strong> (1-28) (0.3 mmol) and hexamethylditin (0.3 mmol) in DME (3 mL) was degassed with nitrogen for 5 minutes. Pd(PPh3 )4 (0.015 mmol) was added and the reaction was heated at 80 0C for 12 hours. The reaction was subsequently cooled to room temperature and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and reduced to dryness. The crude product was purified by flash column chromatography (hexanes : EtOAc = 9 : 1) to afford 5-(trimethylstannyl)-2-phenoxypyrimidine (1-29) as a clear oil. MS (m/z) (M+l)+: 335.0, 337.0. [000266] 5-(Trimethylstannyl)-2-phenoxypyrimidine (1-29) (0.16 mmol) and 5-bromo-2- (2-chloro-6-fluorophenyl)-lH-imidazole-4-carbonitrile (1-10) (0.083 mmol) were dissolved in DME (2 mL) and degassed for 5 minutes with nitrogen. Pd(PPh3)4 (0.0082 mmol) was added and the reaction was heated at 85 0C for 12 hours. The reaction was cooled to room temperature and partitioned with EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered and reduced to dryness. The crude product was purified by flash column chromatography (hexanes : EtOAc = 3 : 1) to afford 2-(2-chloro-6- fluorophenyl)-5-(2-phenoxypyrimidin-5-yl)-lH-imidazole-4-carbonitrile (EX-43) as white glassy solid. 1U NMR (400MEtaz, d4-MeOO) delta 8.95 (s, 2H), 7.50 (m, IH), 7.37 (m, 3H), 7.21 (m, 2H), 7.14 (m, 2H). MS (m/z) (M+l)+: 392.5.

Reference： [1]Patent: WO2010/127152,2010,A2 .Location in patent: Page/Page column 101-102

8
[ 80-48-8 ]
[ 257280-25-4 ]
5-methyl-2-phenoxypyrimidine [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 10180 - 10183

9
[ 5419-55-6 ]
[ 257280-25-4 ]
(2-phenoxypyrimidin-5-yl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The first step: Compound 6 (3 mmol) was dissolved in 15 mL of dried tetrahydrofuran, cooled to -78 C under Ar protection, and n-butyllithium (1.3 mL, 3.3 mmol, 2.5 M in THF) was gradually added dropwise. The reaction was continued at this temperature with stirring for 1 hour. Triisopropyl borate (0.74 g, 3.94 mmol) was then added. After the addition, the reaction was carried out at -78C for 1 hour and then allowed to warm slowly to room temperature.The reaction was quenched with aqueous ammonium chloride solution.The mixture was extracted three times with ethyl acetate, and the combined organic phases were washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Recrystallization of ethyl acetate and petroleum ether afforded a white solid boric acid product which was used directly in the next reaction.

Reference： [1]Patent: CN108069974,2018,A .Location in patent: Paragraph 0245-0248

10
[ 257280-25-4 ]
C₂₀H₂₀N₈O*ClH [ No CAS ]

Reference： [1]Patent: CN108069974,2018,A

11
[ 257280-25-4 ]
C₂₅H₂₈N₈O₃ [ No CAS ]

Reference： [1]Patent: CN108069974,2018,A

12
[ 257280-25-4 ]
(R)-1-(3-(4-amino-3-(2-phenoxypyrimidin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-yl)prop-2-en-1-one [ No CAS ]

Reference： [1]Patent: CN108069974,2018,A

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2h;	General procedure: 3-Chlorophenol (6.0 g, 44.0 mmol), 5-bromo-2-chloropyrimidine (8.1 g, 40.9 mmol) and K2CO3 (45.0 g, 105.0 mmol) are suspended in DMF (30 mL). The resulting mixture is heated for 2 h at 100 C. The suspension is diluted with water and extracted several times with EtOAc. The resulting layers are separated, and the combined organic extracts are washed with saturated aqueous NaCl, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue is purified by silica gel flash column chromatography, using 100% DCM as the eluent, to obtain the title compound (11.0 g, 99% yield). ES/MS m/z (79Br/81Br) 284.8/ 286.8 [M+H].

14
potassium hydrogen difluoride [ No CAS ]
[ 5419-55-6 ]
[ 257280-25-4 ]
potassium trifluoro(2-phenoxypyrimidin-5-yl)boranuide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		<strong>[257280-25-4]5-Bromo-2-phenoxypyrimidine</strong> (Formula 12-2, 412 mg, 1.64 mmol) synthesized in Step 1 was dissolved in THF (10 ml), cooled to -78 C, and 1.6M n-butyl Lithium (1.85 ml, 2.95 mmol, 1.8 eq) was added dropwise. Then, after stirring for 1 hour at the same temperature, triisopropylborate (0.762 ml, 3.28 mmol, 2 eq) was added dropwise at the same temperature. The reaction mixture was stirred at the same temperature for 1 hour, then raised to 0 C. and 4.5M aqueous potassium hydrogendifluoride solution (1.1 ml, 4.92 mmol, 3 eq) was added dropwise. The reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was removed under reduced pressure. Thereafter, the reaction mixture was dissolved in methanol and filtered, and the filtrate was reduced under reduced pressure to obtain a target compound (Formula 12-3).
		<strong>[257280-25-4]5-Bromo-2-phenoxypyrimidine</strong> synthesized in Step 1 (Formula 12-2, 412 mg, 1.64 mmol) was dissolved in THF (10 ml), cooled to -78 C,1.6M n-butyl lithium (1.85 ml, 2.95 mmol, 1.8 eq) was added dropwise. After stirring at the same temperature for 1 hour,Triisopropyl borate (0.762 ml, 3.28 mmol, 2 eq) was added dropwise at the same temperature.After the reaction mixture was stirred at the same temperature for 1 hour,The temperature was raised to 0 C. and a 4.5M aqueous potassium hydrogen difluoride solution (1.1 ml, 4.92 mmol, 3 eq) was added dropwise.The reaction mixture was stirred at room temperature for 1 hour.After completion of the reaction, the solvent was removed under reduced pressure. Thereafter, the reaction mixture was dissolved in methanol, filtered, and the filtrate was reduced in pressure to obtain a target compound (Formula 12-3).

Reference： [1]Patent: KR2019/109007,2019,A .Location in patent: Paragraph 0263; 0267-0269
[2]Patent: KR2020/30970,2020,A .Location in patent: Paragraph 0377; 0381-0383

15
[ 873-74-5 ]
[ 257280-25-4 ]
4-((2-phenoxypyrimidin-5-yl)amino)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; at 120℃; for 1h;Inert atmosphere; Microwave irradiation;	General procedure: A G10 microwave vial equipped with a stir-bar was charged with compound 5-bromo-2-substituted pyrimidine (0.3 mmol), amino compound (0.33 mmol), Pd2dba3 (2 mol%), XPhos (8 mol%), NaOtBu (0.42 mmol) and anhydrous 1,4-dioxane (2 ml). The reaction vial was purged with argon, and heated by microwave irradiation until its temperature was 120 C. Then, the irradiation was automatically controlled to keep the mixture at this temperature for 1h. The reaction mixture was concentrated under reduced pressure and the crude residue was purified by flash chromatography on silica gel. The purified material was dried in vacuo to afford the corresponding products.

Reference： [1]Tetrahedron Letters,2020,vol. 61

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Isomers

Technical Information

• Acetal Formation • Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Convert Haloalkanes into Alcohols by SN2 • Deprotonation of Methylbenzene • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Grignard Reagents Transform Esters into Alcohols • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Alkenes • Halogenation of Benzene • Hiyama Cross-Coupling Reaction • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitration of Benzene • Nomenclature of Ethers • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Preparation of Alkylbenzene • Preparation of Ethers • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reactions of Ethers • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Ring Opening of Oxacyclopropane • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Sulfonation of Benzene • Suzuki Coupling • Synthesis of Alcohols from Tertiary Ethers • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • The Nucleophilic Opening of Oxacyclopropanes • Vilsmeier-Haack Reaction • Williamson Ether Syntheses

Historical Records

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