[ CAS No. 63931-21-5 ] {[proInfo.proName]}

Name: 63931-21-5|5-Bromo-2,4,6-trichloropyrimidine|95%
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SKU: A321427
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Quality Control of [ 63931-21-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 63931-21-5 ]

SDS Specification

Alternatived Products of [ 63931-21-5 ]

Product Details of [ 63931-21-5 ]

CAS No. :	63931-21-5	MDL No. :	MFCD11226676
Formula :	C₄BrCl₃N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GKTWIIVEUYLSCS-UHFFFAOYSA-N
M.W :	262.32	Pubchem ID :	12369426
Synonyms :

Safety of [ 63931-21-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H320-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 63931-21-5 ]

* 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.

Downstream synthetic route of [ 63931-21-5 ]

[ 63931-21-5 ] Synthesis Path-Downstream 1~11

1
[ 27467-92-1 ]
[ 63931-21-5 ]
[ 63931-19-1 ]

Reference： [1]European Journal of Medicinal Chemistry,1977,vol. 12,p. 249 - 256

2
[ 42362-14-1 ]
[ 63931-21-5 ]
[ 63931-17-9 ]

Reference： [1]European Journal of Medicinal Chemistry,1977,vol. 12,p. 249 - 256

4
[ 63931-21-5 ]
[ 3863-11-4 ]
5-bromo-2,6-dichloro-N-(3,4-difluorophenyl)pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium acetate; In tetrahydrofuran; water; at 20 - 25℃; for 18h;	5-Bromo-2,4,6-trichloropyrimidine (3.00 g, 10.9 mmol) was dissolved in THF (18 mL) and water (9 mL), and sodium acetate (2.67 g, 32.6 mmol), followed by 3,4-difluoroaniline (1.43 g, 1.10 mL, 11.1 mmol) were added. The mixture was stirred at room temperature for 18 h. After that, a saturated aqueous solution of sodium hydrogencarbonate (30 mL) was added and the resulting mixture was extracted with ethyl acetate (2 x 150 mL). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 120 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 10:90) to afford, after drying in vacuo (40C, 5 mbar), the title compound as a light yellow solid (3.32 g, 86%). HPLC (method LCMS_fastgradient) tR = 1.37 min. 1H NMR (CDC13, 300 MHz): delta 7.17- 7.24 (m, 2 H), 7.43 (br s, 1 H), 7.59-7.68 (m, 1 H). MS (ES+) m/z 353.9, 355.9, 357.8 [M+H, Br & 2 CI isotopes] .

Reference： [1]Patent: WO2018/11164,2018,A1 .Location in patent: Page/Page column 29

5
[ 367-25-9 ]
[ 63931-21-5 ]
5-bromo-2,6-dichloro-N-(2,4-difluorophenyl)pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium acetate; In tetrahydrofuran; water; at 20 - 25℃; for 18h;	5-Bromo-2,4,6-trichloropyrimidine (2.50 g, 9.05 mmol) was dissolved in THF (16 mL) and water (8 mL), and sodium acetate (2.23 g, 27.2 mmol), followed by 2,4-difluoroaniline (1.18 g, 0.92 mL, 9.14 mmol) were added. The mixture was stirred at room temperature for 18 h. After that, a saturated aqueous solution of sodium hydrogencarbonate (30 mL) was added and the resulting mixture was extracted with ethyl acetate (2 x 150 mL). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 120 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 5:95) to yield, after drying in vacuo (40C, 5 mbar), the title compound as an off-white solid (2.22 g, 69%). HPLC (method LCMS_fastgradient) tR = 1.39 min. 1H NMR (CDC13, 300 MHz): delta 6.91- 7.03 (m, 2 H), 7.56 (br s, 1 H), 8.16 (ddd, 7 = 5.8, 9.7, 9.7 Hz, 1 H). MS (ES+) m/z 353.9, 355.9, 357.9 [M+H, Br & 2 CI isotopes].

Reference： [1]Patent: WO2018/11164,2018,A1 .Location in patent: Page/Page column 31

6
[ 637031-93-7 ]
[ 63931-21-5 ]
5-bromo-2,6-dichloro-N-(3,3-difluorocyclobutyl)pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 - 25℃; for 7h;	5-Bromo-2,4,6-trichloropyrimidine (1.28 g, 4.88 mmol) and 3,3-difluorocyclobutan- amine hydrochloride (715 mg, 4.98 mmol) were suspended in acetonitrile (6 mL) and N,N- diisopropylethylamine (1.55 g, 2.1 mL, 12 mmol) was added at room temperature. The resulting yellow solution was stirred for 7 h at room temperature. After that, the reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (silica gel, 80 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 10:90) to yield, after drying in vacuo (40C, 5 mbar), the title compound as a pale yellow oil (1.188 g, 73%). HPLC (method (0254) LCMS_fastgradient) tR = 1.31 min. 1H NMR (CDC13, 300 MHz): delta 2.48-2.67 (m, 2 H), 3.08-3.25 (m, 2 H), 4.39-4.53 (m, 1 H), 5.78-5.90 (m, 1 H). MS (ES+) m/z 330.0, 332.0, 334.0 [M+H, Br & 2 CI isotopes] .

Reference： [1]Patent: WO2018/11164,2018,A1 .Location in patent: Page/Page column 33

7
[ 262852-11-9 ]
[ 63931-21-5 ]
5-bromo-2,6-dichloro-N-(3-(trifluoromethyl)bicyclo[1.1.1]pentan-1-yl)pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 - 25℃; for 7h;	5-Bromo-2,4,6-trichloropyrimidine (1.30 g, 4.96 mmol) and 3-(trifluoromethyl)- bicyclo[l.l. l]pentan-l- amine hydrochloride (985 mg, 4.99 mmol) were suspended in acetonitrile (6.5 mL) and N,N-diisopropylethylamine (1.55 g, 2.1 mL, 12 mmol) was added at room temperature. The resulting yellow solution was stirred for 7 h at room temperature. After that, the reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (silica gel, 80 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 10:90) to yield, after drying in vacuo (40C, 5 mbar), the title compound as an off-white solid (1.487 g, 80%). HPLC (method LCMS_fastgradient) tR = 1.50 min. 1H NMR (CDC13, 300 MHz): delta 2.46 (s, 6 H), 6.10 (br s, 1 H). MS (ES+) m/z 375.9, 377.9, 379.8 [M+H, Br & 2 CI isotopes].

Reference： [1]Patent: WO2018/11164,2018,A1 .Location in patent: Page/Page column 35

8
4-fluoro-N-(3-methylbut-3-en-1-yl)aniline [ No CAS ]
[ 63931-21-5 ]
5-bromo-2,6-dichloro-N-(4-fluorophenyl)-N-(3-methylbut-3-en-1-yl)pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With sodium acetate; In tetrahydrofuran; water; at 20 - 25℃; for 18h;	4-Fluoro-N-(3-methylbut-3-en-l-yl)aniline (Int-24, 382 mg, 2.13 mmol) was dissolved in (0285) THF (4 mL) and water (2 mL), and sodium acetate (525 mg, 6.39 mmol), followed by 5-bromo- 2,4,6-trichloropyrimidine (589 mg, 2.13 mmol) were added. The mixture was stirred at room temperature for 18 h. After that, a saturated aqueous solution of sodium hydrogencarbonate (10 mL) was added and the resulting mixture was extracted with ethyl acetate (2 x 80 mL). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 40 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 5:95) to yield, after drying in vacuo (40C, 5 mbar), the title compound as a yellow solid (527 mg, 61 ). HPLC (method LCMS_fastgradient) tR = 1.70 min. 1H NMR (CDC13, 300 MHz): delta 1.79 (s, 3 H), 2.32-2.40 (m, 2 H), 4.01-4.08 (m, 2 H), 4.67-4.71 (m, 1 H), 4.78-4.82 (m, 1 H), 7.06-7.11 (m, 4 H). MS (ES+) m/z 404.1, 406.1, 408.1 [M+H, Br & 2 CI isotopes].

Reference： [1]Patent: WO2018/11164,2018,A1 .Location in patent: Page/Page column 38; 39

9
[ 4519-40-8 ]
[ 63931-21-5 ]
5-bromo-2,6-dichloro-N-(2,3-difluorophenyl)pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium acetate; In tetrahydrofuran; water; at 20 - 25℃; for 18h;	5-Bromo-2,4,6-trichloropyrimidine (2.30 g, 8.33 mmol) was dissolved in THF (14 mL) and water (7 mL), and sodium acetate (2.05 g, 25.0 mmol), followed by 2,3-difluoroaniline (1.15 g, 0.90 mL, 8.7 mmol) were added. The mixture was stirred at room temperature for 18 h. After that, a saturated aqueous solution of sodium hydrogencarbonate (20 mL) was added and the resulting mixture was extracted with ethyl acetate (2 x 100 mL). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 80 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 10:90) to yield, after drying in vacuo (40C, 5 mbar), the title compound as a light brown solid (1.23 g, 42%). HPLC (method LCMS_fastgradient) tR = 1.38 min. 1H NMR (CDC13, 300 MHz): delta 6.97- 7.09 (m, 1 H), 7.13-7.23 (m, 1 H), 7.72 (br s, 1 H), 8.03-8.11 (m, 1 H). MS (ES+) m/z 353.8, 355.8, 357.8 [M+H, Br & 2 CI isotopes].

Reference： [1]Patent: WO2018/11164,2018,A1 .Location in patent: Page/Page column 45; 46

10
[ 2106-02-7 ]
[ 63931-21-5 ]
5-bromo-2,6-dichloro-N-(2-chloro-4-fluorophenyl)pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		2-Chloro-4-fluoroaniline (512 mg, 0.42 mL, 3.45 mmol) was dissolved in THF (10 mL), the solution was cooled to 0-5C (ice bath) and a solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran / ethylbenzene (1.0 M, 3.4 mL, 3.4 mmol) was added. After stirring for 15 min at 0-5C, a solution of <strong>[63931-21-5]5-bromo-2,4,6-trichloropyrimidine</strong> (900 mg, 3.26 mmol) in tetrahydrofuran (7 mL) was added dropwise. The reaction mixture was stirred for 18 h at room temperature. During that period, two additional portions of a solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran / ethylbenzene (1.0 M, 1.7 mL & 0.82 mL, 1.7 mmol & 0.82 mmol) were added at 0-5C after 45 min and 2 h, respectively. Then, water (10 mL) and a saturated aqueous solution of ammonium chloride (30 mL) were added and the resulting mixture was extracted with ethyl acetate (2 x 150 mL). The organic layers were washed with water (15 mL) and brine (15 mL), combined, dried (sodium sulfate) and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 40 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 5:95) to yield, after drying in vacuo (40C, 5 mbar), the title compound as an off-white solid (956 mg, 79%). HPLC (method LCMS_fastgradient) tR = 1.47 min. 1H NMR (CDC13, 300 MHz): delta 7.08-7.16 (m, 1 H), 7.24 (dd, / = 2.8, 7.9 Hz, 1 H), 7.99 (br s, 1 H), 8.33 (dd, / = 5.4, 9.3 Hz, 1 H). MS (ES+) m/z 370.0, 372.0, 374.0 [M+H, Br & 3 CI isotopes].

Reference： [1]Patent: WO2018/11164,2018,A1 .Location in patent: Page/Page column 47; 48

11
[ 371-40-4 ]
[ 63931-21-5 ]
5-bromo-2,6-dichloro-N-(4-fluorophenyl)pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium acetate; In tetrahydrofuran; water; at 20 - 25℃; for 18h;	5-Bromo-2,4,6-trichloropyrimidine (1.880 g, 6.81 mmol) was dissolved in THF (11 mL) and water (5 mL), and sodium acetate (1.68 g, 20.4 mmol), followed by 4-fluoroaniline (787 mg, 0.68 mL, 6.87 mmol) were added. The mixture was stirred at room temperature for 18 h. After that, a saturated aqueous solution of sodium hydrogencarbonate (15 mL) was added and the resulting mixture was extracted with ethyl acetate (2 x 150 mL). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 40 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 10:90) to afford, after drying in vacuo (40C, 5 mbar), the title compound as a light brown solid (2.07 g, 90%). HPLC (method LCMS_fastgradient) tR = 1.36 min. 1H NMR (CDC13, 300 MHz): delta 7.12 (dd, / = 8.3, 9.1 Hz, 2 H), 7.43 (br s, 1 H), 7.52 (dd, / = 4.6, 8.9 Hz, 2 H). MS (ES+) m/z 335.9, 337.9, 339.9 [M+H, Br & 2 CI isotopes] .
90%	With sodium acetate; In tetrahydrofuran; water; at 20℃; for 18h;	5-Bromo-2,4,6-trichloropyrimidine (1.880 g, 6.81 mmol) was dissolved in THF (11 mF) and water (5 mF), and sodium acetate (1.68 g, 20.4 mmol), followed by 4-fluoroaniline (787 mg, (0231) 0.68 mF, 6.87 mmol) were added. The mixture was stirred at room temperature for 18 h. After that, a saturated aqueous solution of sodium hydrogenocarbonate (15 mF) was added and the resulting mixture was extracted with ethyl acetate (2 x 150 mF). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 40 g, eluting with ethyl acetate / n-heptane, gradient 0:100 to 10:90) to afford, after drying in vacuo (40C, 5 mbar), the title compound as a light brown solid (2.07 g, 90%). MS (ES+) m/z 335.9, 337.9, 339.9 [M+H, Br & 2 Cl isotopes].

Reference： [1]Patent: WO2018/11164,2018,A1 .Location in patent: Page/Page column 27
[2]Patent: WO2019/101984,2019,A1 .Location in patent: Page/Page column 20

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Ghs Precautionary Statements

Precautionary Statements-General
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P101	If medical advice is needed,have product container or label at hand.
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Prevention
Code	Phrase
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P281	Use personal protective equipment as required.
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Response
Code	Phrase
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P320
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P321
P322
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P342	If experiencing respiratory symptoms:
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
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P422
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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. 63931-21-5 ] {[proInfo.proName]}

Quality Control of [ 63931-21-5 ]

Related Doc. of [ 63931-21-5 ]

Product Details of [ 63931-21-5 ]

Safety of [ 63931-21-5 ]

Application In Synthesis of [ 63931-21-5 ]

[ 63931-21-5 ] Synthesis Path-Downstream 1~11

Pharmaceutical Intermediates of [ 63931-21-5 ]

Etravirine Intermediates

Related Functional Groups of [ 63931-21-5 ]

Bromides

Chlorides

Related Parent Nucleus of [ 63931-21-5 ]

Pyrimidines

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[ 63931-21-5 ]

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[ 63931-21-5 ]

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[ 63931-21-5 ]