[ CAS No. 1352796-65-6 ] {[proInfo.proName]}

Name: 1352796-65-6|2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine|95%
Brand: Ambeed
SKU: A881738
Rating: 95 (27 reviews)

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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 1352796-65-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1352796-65-6 ]

Product Details of [ 1352796-65-6 ]

CAS No. :	1352796-65-6	MDL No. :	MFCD13182191
Formula :	C₁₀H₁₄BFN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XFNGULIUEUPWIG-UHFFFAOYSA-N
M.W :	224.04	Pubchem ID :	72219099
Synonyms :

Safety of [ 1352796-65-6 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501	UN#:	2811
Hazard Statements:	H301-H311-H331	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1352796-65-6 ]

* 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 [ 1352796-65-6 ]

[ 1352796-65-6 ] Synthesis Path-Downstream 1~6

1
[ 869494-16-6 ]
[ 1352796-65-6 ]
[ 2222758-57-6 ]

Yield	Reaction Conditions	Operation in experiment
12%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	tert-butyl 3 -(5-(4,4,5, 5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyrimidin-2-yl)-3 ,6- diazabicyclo[3. 1.1 ]heptane-6-carboxylate A mixture of 2-fluoro-5 -(4,4,5,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyrimidine (0.311 g, 1.39 mmol), tert-butyl 3 ,6-diazabicyclo[3. 1.1 ]heptane-6-carboxylate (0.303 g, 1.53 mmol) and DIEA (0.484 mL, 2.78 mmol) in DMF (9.25 mL) was stirred overnight at ambient temperature. The reaction mixture was worked up with EtOAc and water. The organic layer was washed with water and brine, then dried (Na2504), filtered and concentrated. The residue was purified by silica chromatography (10-90% EtOAc in hexanes) to afford the title compound (68 mg, 12% yield).

Reference： [1]Current Patent Assignee: PFIZER INC; ELI LILLY & CO - WO2018/71447, 2018, A1 Location in patent: Paragraph 001278; 001279; 001280

2
[ 1352796-65-6 ]
[ 2223058-74-8 ]
[ 2223058-73-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,4-dioxane; water at 95℃; for 3h; Inert atmosphere;

Reference： [1]Pike, Kurt G.; Barlaam, Bernard; Cadogan, Elaine; Campbell, Andrew; Chen, Yingxue; Colclough, Nicola; Davies, Nichola L.; De-Almeida, Camila; Degorce, Sebastien L.; Didelot, Myriam; Dishington, Allan; Ducray, Richard; Durant, Stephen T.; Hassall, Lorraine A.; Holmes, Jane; Hughes, Gareth D.; Macfaul, Philip A.; Mulholland, Keith R.; McGuire, Thomas M.; Ouvry, Gilles; Pass, Martin; Robb, Graeme; Stratton, Natalie; Wang, Zhenhua; Wilson, Joanne; Zhai, Baochang; Zhao, Kang; Al-Huniti, Nidal [Journal of Medicinal Chemistry, 2018, vol. 61, # 9, p. 3823 - 3841]

3
[ 163271-08-7 ]
2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine [ No CAS ]
tert-butyl (1-(5-(3-cyano-6-(2-morpholinoethoxy)pyrazolo[1,5-a]pyridin-4-yl)pyrimidin-2-yl)-4-methylpiperidin-4-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In 1,4-dioxane; at 60℃;Sealed tube;	Preparation of (2-(4-((tert-butoxycarbonyl)amino)-4-methylpiperidin-l- vDpyrimidin-5-vDboronic acid. In a pressure vessel, a mixture of tert-butyl (4- methylpiperidin-4-yl)carbamate (0.23 g, 1.1 mmol), 2-fluoro-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)pyrimidine (0.2 g, 0.89 mmol) and K2CCb(s) (0.62 g, 4.5 mmol) was combined in dioxane (8.9 mL), and the vessel was sealed. The reaction mixture was stirred overnight at 60 C. After cooling to ambient temperature, the reaction mixture was directly used for the next step assuming quantitative yield. MS (apci) m/z = 337.2 (M+H).

Reference： [1]Patent: WO2018/71454,2018,A1 .Location in patent: Paragraph 001248; 001250

4
[ 163271-08-7 ]
2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine [ No CAS ]
tert-butyl (4-methyl-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)piperidin-4-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In 1,4-dioxane; at 60℃;Inert atmosphere; Sealed tube;	In a pressure vessel, a mixture of <strong>[163271-08-7]tert-butyl (4-methylpiperidin-4-yl)carbamate</strong> (0.23 g, 1.1 mmol), 2-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidine (0.2 g, 0.89 mmol) and K2CCb(s) (944 mg, 9.62 mmol) was combined in dioxane (8.9 mL). The vessel was sealed, and the reaction mixture was stirred overnight at 60 C. After cooling to ambient temperature, the reaction mixture was preserved as a suspension (i.e. without further work up, purification or isolation) containing the title compound (assumed 370 mg, quantitative yield. MS (apci) m/z = 419.3 (M+H).

Reference： [1]Patent: WO2018/71454,2018,A1 .Location in patent: Paragraph 001475; 001476; 001477

5
[ 1166997-21-2 ]
[ 1352796-65-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,2-dimethoxyethane; water at 95℃; for 2h; Sealed tube; Inert atmosphere;	Intermediate L: Synthesis of 3-(3-((2-chloropyrimidin-5-yl)methyl)isoxazol-5-yl)pyridin-2-amine 2-fhioro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidine (l.OOg, 4.44mmol) and di- tert-butyl [3-(3-(chloromethyl)-l,2-oxazol-5-yl)pyridin-2-yl]imidodicarbonate (Intermediate A, 2.00g, 4.88mmol) were mixed with DME (l5mL) in a sealable tube. A 2M solution of sodium carbonate in water (5 55mL, 11.09mmol) and palladium tetrakis triphenylphosphine (0.36g, 0.3 lmmol) were added and the sealable tube was flushed with argon and sealed. The mixture was stirred for 2h at 95°C. The cooled reaction mixture was poured into ethyl acetate (500mL), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Si02, hexane/ethyl acetate) to give the di-Boc protected coupling intermediate, to which was added formic acid (8mL). The resulting mixture was stirred for l3h at 2l-25°C to complete the di-Boc de -protection. During this step the fluoropyridine also completely hydrolyzed. Toluene (lOOmL) and acetonitrile (50mL) were added and all volatiles were removed under reduced pressure. This addition/evaporation procedure was repeated three times to complete the removal of formic acid and to obtain a solid residue of (5-((5-(2-aminopyridin-3-yl)isoxazol-3-yl)methyl)pyrimidin-2-ol (570mg, 2T2mmol). The residue was suspended in acetonitrile (2mL). N-benzyl-N,N-diethylethanaminium chloride (237mg, l.04mmol) and phosphoryl trichloride (0.58mL, 6.24mmol) were added, followed by the addition of N-ethyl-N- isopropylpropan-2 -amine (0.7lmL, 4. l6mmol). The mixture was heated in a sealed tube at 90°C for 20h and then slowly added to a stirred solution of NaHC03 in water. Some ice was added to maintain a temperature around 30°C. After quenching was complete, the mixture was extracted with EtOAc. The combined organic layers were dried and concentrated under reduced pressure to obtain the crude product (3-(3-((2-chloropyrimidin-5-yl)methyl)isoxazol-5-yl)pyridin-2-amine (l80mg, 0.63mmol, 13% overall yield)) as a solid, which was directly used in the following experiments without further purification. 500 MHz 1H NMR (DMSO-d6) 5 8.80 (s, 2H), 8.10 (dd, J= 4.8, 1.9 Hz, 1H), 7.86 (dd, .7= 7.7, 1.9 Hz, 1H), 6.89 (s, 1H), 6.71 (dd, J= 7.7, 4.8 Hz, 1H), 6.28 (s, 2H), 4.15 (s, 2H). MS: 287.9 [M+H]+.

Reference： [1]Current Patent Assignee: PFIZER INC - WO2019/113542, 2019, A1 Location in patent: Paragraph 0337

6
[ 1166997-21-2 ]
[ 1352796-65-6 ]
[ 2342610-52-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water at 95℃; for 2h; Sealed tube; Inert atmosphere;	Intermediate L: Synthesis of 3-(3-((2-chloropyrimidin-5-yl)methyl)isoxazol-5-yl)pyridin-2-amine -fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (1.00g, 4.44mmol) and di- tert-butyl [3-(3-(chloromethyl)-1,2-oxazol-5-yl)pyridin-2-yl]imidodicarbonate (Intermediate A, 2.00g, 4.88mmol) were mixed with DME (15mL) in a sealable tube. A 2M solution of sodium carbonate in water (5.55mL, 11.09mmol) and palladium tetrakis triphenylphosphine (0.36g, 0.31mmol) were added and the sealable tube was flushed with argon and sealed. The mixture was stirred for 2h at 95°C. The cooled reaction mixture was poured into ethyl acetate (500mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, hexane/ethyl acetate) to give the di-Boc protected coupling intermediate, to which was added formic acid (8mL). The resulting mixture was stirred for 13h at 21-25°C to complete the di-Boc de-protection. During this step the fluoropyridine also completely hydrolyzed. Toluene (100mL) and acetonitrile (50mL) were added and all volatiles were removed under reduced pressure. This addition/evaporation procedure was repeated three times to complete the removal of formic acid and to obtain a solid residue of (5-((5-(2-aminopyridin-3-yl)isoxazol-3-yl)methyl)pyrimidin-2-ol (570mg, 2.12mmol). The residue was suspended in acetonitrile (2mL). N-benzyl-N,N-diethylethanaminium chloride (237mg, 1.04mmol) and phosphoryl trichloride (0.58mL, 6.24mmol) were added, followed by the addition of N-ethyl-N- isopropylpropan-2-amine (0.71mL, 4.16mmol). The mixture was heated in a sealed tube at 90°C for 20h and then slowly added to a stirred solution of NaHCO3 in water. Some ice was added to maintain a temperature around 30°C. After quenching was complete, the mixture was extracted with EtOAc. The combined organic layers were dried and concentrated under reduced pressure to obtain the crude product (3-(3-((2-chloropyrimidin-5-yl)methyl)isoxazol-5-yl)pyridin-2-amine (180mg, 0.63mmol, 13% overall yield)) as a solid, which was directly used in the following experiments without further purification. 500 MHz 1H NMR (DMSO-d6) d 8.80 (s, 2H), 8.10 (dd, J = 4.8, 1.9 Hz, 1H), 7.86 (dd, J = 7.7, 1.9 Hz, 1H), 6.89 (s, 1H), 6.71 (dd, J = 7.7, 4.8 Hz, 1H), 6.28 (s, 2H), 4.15 (s, 2H). MS: 287.9 [M+H]+.

Reference： [1]Current Patent Assignee: PFIZER INC - WO2020/247804, 2020, A1 Location in patent: Paragraph 0347

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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
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
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
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
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. 1352796-65-6 ] {[proInfo.proName]}

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[ 1352796-65-6 ] Synthesis Path-Downstream 1~6

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Organoboron

Esters

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Pyrimidines

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