76661-24-0|2,5-Dichloro-4-(3-nitrophenoxy)pyrimidine| Ambeed

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Quality Control of [ 76661-24-0 ] Purity: 97% SDS Specification

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Product Details of [ 76661-24-0 ]

CAS No. :	76661-24-0
Formula :	C₁₀H₅Cl₂N₃O₃
M.W :	286.07
SMILES Code :	O=[N+](C1=CC(OC2=NC(Cl)=NC=C2Cl)=CC=C1)[O-]
MDL No. :	MFCD22124565
InChI Key :	SEGZIOXGXFJLHD-UHFFFAOYSA-N
Pubchem ID :	12679950

Safety of [ 76661-24-0 ]

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

Application In Synthesis of [ 76661-24-0 ]

* 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 [ 76661-24-0 ]

[ 76661-24-0 ] Synthesis Path-Downstream 1~35

1
[ 100-02-7 ]
[ 5750-76-5 ]
[ 76661-24-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2.0h;	2,5-dichloro-4-(3-nitrophenoxy)pyrimidine Potassium carbonate (2.42 g, 17.5 mmol) and 2,4,5-trichloropyrimidine (1.0 mL, 8.72 mmol) were added to the solution of 3-nitrophenol (1.21 g, 8.72 mmol) in DMF (20 mL). The reaction was heated to 6O0C for 2 h. The reaction mixture was filtered, the filtrate was dilute with ethyl acetate and washed with water (20 mL) three times. The organic layer wad dried over anhydrous sodium sulfate and concentrated to afford 2.24 g (90%) of a light yellow solid, which was used without further purification. 1H NMR 600 MHz (DMSO d6) δ 8.87 (s, IH), 8.28 (m, IH), 8.21 (m, IH), 7.84 (m, 2H); MS m/z: 287.07 (M+1).

References: [1]Patent: WO2010/129053,2010,A2 .Location in patent: Page/Page column 122-123.

2
[ 122833-04-9 ]
[ 76661-24-0 ]
[ 1213269-25-0 ]

Yield	Reaction Conditions	Operation in experiment
81%		5-chloro-N-(2-methoxy-4-(4-methyIpiperazin-l-yl)phenyl)-4-(3-nitrophenoxy)pyrimidin- 2-amine A flask was charged with <strong>[76661-24-0]2,5-dichloro-4-(3-nitrophenoxy)pyrimidine</strong> (1.56 g, 5.45 mmol), 2-methoxy-4-(4-methylpiperazin-l-yl)benzenamine (1.21 g, 5.45 mmol), TFA ( 0.42 mL, 5.45 mmol uL), 2-BuOH (30 mL). The slurry was heated to 1000C for 2h. The reaction mixture was allowed to cool to room temperature and, was neutralized with a saturated aqueous sodium bicarbonate solution. The aqueous mixture was then extracted with ethyl acetate (50 mL) three times. The crude product was purified using flash chromatography with 30: 1 :0.3 (v/v/v) dichloromethane-methanol-triethylamine to afford 2.07 g brown solid (81%). 1H NMR 600 MHz (DMSO d6) δ 8.38 (s, IH), 8.28 (s, IH), 8.16 (m, 2H), 7.76 (m, 2H), 7.08 (s, I H), 6.46 (m, IH), 6.14 (m, I H), 3.72 (s, 3H), 3.33 (m, 4H), 3.05 (m, 4H), 2.28 (s, 3H); MS m/z: 471.91 (M+1).
75%	With trifluoroacetic acid; In iso-butanol; at 100℃; for 4.0h;	General procedure: To a mixture of pyrimidine analogues 34, 35 or 36 (1.56 g, 5.45 mmol), amino piperazine 38 (1.21 g, 5.45 mmol) and anhydrous 2-butanol (30 mL) was added trifluoroacetic acid (0.42 mL, 5.45 mmol). The reaction mixture was heated to 100 C and stirred for 4 h. Subsequently, it was cooled to room temperature and was basified (pH 8.0) by dropwise addition of saturated aqueous sodium bicarbonate solution. The 2-butanol was removed in vacuo to obtain a thick slurry which was dissolved in ethyl acetate (50 mL). The organic layer was washed with water (3 x 20 mL) and brine (1 x 20 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash silica gel chromatography using dichloromethane-methanol (25:1, v/v) as eluent to afford the nitro analogues as brown solids in yields ranging from 72 - 79%.
72%	With trifluoroacetic acid; In iso-butanol; for 5.0h;Reflux;	To a solution of <strong>[76661-24-0]2,5-dichloro-4-(3-nitrophenoxy)pyrimidine</strong> (0.9 g, 3.16 mmol), 2-methoxy-4-(4-methylpiperazin-1-yl)benzenamine (0.7 g, 3.16 mmol), in 2-butanol (20 mL) was added trifluoroacetic acid (0.25 mL, 3.16 mmol). The resultant slurry was refluxed for 5 hours. The reaction mixture was allowed to cool to room temperature and then was neutralized with a saturated aqueous sodium bicarbonate solution. The aqueous mixture was then extracted with ethyl acetate (3*500 mL) and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to furnish an oil which was purified by column chromatography on silica gel (100-200 mesh) eluting with 2-3% (v/v) methanol in dichloromethane to produce as pale brown solid (1 g, yield 72%). 1H NMR 400 MHz (DMSO-d6) δ 8.37 (s, 1H), 8.29 (s, 1H), 8.17-8.16 (m, 2H), 7.75-7.74 (m, 2H), 7.08-7.06 (m, 1H), 6.48 (s, 1H), 6.14 (s, br, 1H), 3.69 (s, 3H), 3.03 (t, J=4.8 Hz, 4H), 2.46 (t, J=4.8 Hz, 4H), 2.23 (s, 3H); LCMS m/e: 471 [M+1]+.

65%

With trifluoroacetic acid; In butan-1-ol; at 100℃; for 18.0h;

To a solution of compound 8 (1.33 g, 4.66 mmol) and compound11 (1.03 g, 4.66 mmol) in anhydrous 1-butanol (20 mL), trifluoroacetic acid (0.36 mL, 4.66 mmol) was added. The reaction mixturewas heated to 100 C and stirred for 18 h. Subsequently, it wascooled to room temperature and saturated aqueous sodium bicarbonatesolution was added drop wise until basic pH was obtained.The volatiles were removed in vacuo and the obtained thick slurrywas dissolved in DCM (50 mL). The organic layer was washed withwater (20 mL), brine (20 mL), dried over anhydrous sodium sulfate,filtered and concentrated in vacuo. The crude was purified by flashsilica gel chromatography using DCM/MeOH (96:4, v/v) as eluentto afford 1.42 g of the desired product 12 (3.02 mmol, 65%) as white solid.

References: [1]Patent: WO2010/129053,2010,A2 .Location in patent: Page/Page column 123.
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4832 - 4837.
[3]Patent: US2018/208564,2018,A1 .Location in patent: Paragraph 0381-0382.
[4]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 2767 - 2780.
[5]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.
[6]European Journal of Medicinal Chemistry,2014,vol. 77,p. 75 - 83.

3
[ 1246532-96-6 ]
[ 76661-24-0 ]
[ 1254783-97-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tris-(dibenzylideneacetone)dipalladium(0); XPhos; In iso-butanol; at 90℃; for 2.0h;	tert-butyl 4-(4-(5-chloro-4-(3-nitrophenoxy)pyrimidin-2-ylamino)-3- methoxyphenyl)piperazine-l-carboxylate A flask was charged with 2,5-dichloro-4-(3- nitrophenoxy)pyrimidine (200mg, 0.7mmol), tert-butyl 4-(4-amino-3- methoxyphenyl)piperazine-l-carboxylate (215mg, 0.7mmol), Pd2(dba)3(64mg, 0.07mmol)), X-Phos (33 mg, 0.07mmol), potassium carbonate (200mg, 1.4mmol) in 2-BuOH (1OmL). The mixture was degased and heated to 9O0C for 2 hours. The slurry was filtrated through celite and washed with ethyl acetate. The concentrated residue was purified by flash chromatography to afford the title compound. MS(M+1): 558.0.

References: [1]Patent: WO2010/129053,2010,A2 .Location in patent: Page/Page column 127-128.

4
[ 209960-91-8 ]
[ 76661-24-0 ]
5-chloro-N-(2-methoxy-4-morpholinophenyl)-4-(3-nitrophenoxy)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.2%	With trifluoroacetic acid; In iso-butanol; at 100℃;	General procedure: To a solution of 3a-r (1.50 mmol, 1 eq) and 6a-b (1.50 mmol, 1eq) in 2-BuOH (8 mL) were added TFA (2 mL). The slurrywas heatedto 100 C for 2e3 h. The reaction mixture was allowed to cool toroom temperature and was neutralized with a saturated aqueoussodium bicarbonate solution. The mixture was then extracted withethyl acetate (50 mL) three times. The crude was purified by flashchromatography with 25:1 (v/v) dichloromethane - methanol.

References: [1]European Journal of Medicinal Chemistry,2021,vol. 210.
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

5
2-methoxy-4-[4-(4-methylpiperazin-1-yl)-piperidin-1-yl]-phenylamine [ No CAS ]
[ 76661-24-0 ]
C₂₇H₃₂ClN₇O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

6
[ 694499-26-8 ]
[ 76661-24-0 ]
C₂₃H₂₂ClF₃N₆O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

7
[ 761440-87-3 ]
[ 76661-24-0 ]
C₂₂H₂₂ClN₅O₅ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

8
[ 1116228-62-6 ]
[ 76661-24-0 ]
C₂₃H₂₄ClN₅O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

9
[ 1124330-14-8 ]
[ 76661-24-0 ]
C₂₃H₂₄ClN₅O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

10
[ 76661-24-0 ]
C₁₃H₁₈N₂O [ No CAS ]
C₂₃H₂₂ClN₅O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

11
2-(4-aminophenyl)-1-(4-methylpiperazin-1-yl)ethanone [ No CAS ]
[ 76661-24-0 ]
C₂₃H₂₃ClN₆O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

12
[ 76661-24-0 ]
[ 1233094-59-1 ]
C₂₃H₂₃ClN₆O₅ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

13
[ 76661-24-0 ]
[ 1001346-50-4 ]
C₂₄H₂₅ClN₆O₆ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

14
[ 50534-11-7 ]
[ 76661-24-0 ]
C₂₃H₂₃ClN₆O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

15
[ 876126-60-2 ]
[ 76661-24-0 ]
C₂₄H₂₅ClN₆O₅ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

16
[ 76661-24-0 ]
[ 1265526-86-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

17
[ 76661-24-0 ]
[ 1265526-88-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

18
[ 76661-24-0 ]
C₁₇H₁₄ClFN₄O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

19
[ 76661-24-0 ]
C₂₂H₁₈ClN₅O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

20
[ 76661-24-0 ]
4-(3-aminophenoxy)-5-chloro-N-(2-methoxy-4-morpholinophenyl)pyrimidin-2-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.
[2]European Journal of Medicinal Chemistry,2021,vol. 210.

21
[ 76661-24-0 ]
C₂₂H₂₄ClN₅O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

22
[ 76661-24-0 ]
[ 1254783-32-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

23
[ 76661-24-0 ]
C₂₃H₂₆ClN₅O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

24
[ 76661-24-0 ]
C₂₃H₂₆ClN₅O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

25
[ 76661-24-0 ]
C₂₃H₂₄ClN₅O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

26
[ 76661-24-0 ]
[ 1265527-57-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.
[2]European Journal of Medicinal Chemistry,2021,vol. 210.

27
[ 76661-24-0 ]
[ 1213269-26-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.
[2]European Journal of Medicinal Chemistry,2014,vol. 77,p. 75 - 83.
[3]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 2767 - 2780.
[4]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4832 - 4837.
[5]Patent: US2018/208564,2018,A1 .

28
[ 76661-24-0 ]
C₂₇H₃₄ClN₇O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

29
[ 76661-24-0 ]
C₂₃H₂₅ClN₆O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

30
[ 76661-24-0 ]
C₂₃H₂₅ClN₆O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

31
[ 76661-24-0 ]
C₂₄H₂₇ClN₆O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

32
[ 76661-24-0 ]
C₂₃H₂₅ClN₆O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

33
[ 76661-24-0 ]
[ 1254783-16-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

34
[ 76661-24-0 ]
C₂₄H₂₇ClN₆O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

35
[ 76661-24-0 ]
C₂₂H₂₅ClN₆O [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643.

Historical Records

Technical Information

• Alkyl Halide Occurrence • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Nomenclature of Ethers • Preparation of Alkylbenzene • Preparation of Ethers • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Vilsmeier-Haack Reaction

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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

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CAS No.: 76661-24-0

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CAS No.: 76661-24-0

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[ 76661-24-0 ] Synthesis Path-Downstream 1~35

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