[ CAS No. 76661-24-0 ] {[proInfo.proName]}

Name: 76661-24-0|2,5-Dichloro-4-(3-nitrophenoxy)pyrimidine|97%
Brand: Ambeed
SKU: A708006
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Quality Control of [ 76661-24-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 76661-24-0 ]

Product Details of [ 76661-24-0 ]

CAS No. :	76661-24-0	MDL No. :	MFCD22124565
Formula :	C₁₀H₅Cl₂N₃O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SEGZIOXGXFJLHD-UHFFFAOYSA-N
M.W :	286.07	Pubchem ID :	12679950
Synonyms :

Calculated chemistry of [ 76661-24-0 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	67.39
TPSA :	80.83 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.21
Log Po/w (XLOGP3) :	3.48
Log Po/w (WLOGP) :	3.48
Log Po/w (MLOGP) :	2.28
Log Po/w (SILICOS-IT) :	1.06
Consensus Log Po/w :	2.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.1
Solubility :	0.0227 mg/ml ; 0.0000792 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.86
Solubility :	0.00395 mg/ml ; 0.0000138 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.52
Solubility :	0.00868 mg/ml ; 0.0000303 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.55

Safety of [ 76661-24-0 ]

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

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.

Upstream synthesis route of [ 76661-24-0 ]
Downstream synthetic route of [ 76661-24-0 ]

[ 76661-24-0 ] Synthesis Path-Upstream 1~1

1
[ 76661-24-0 ]
[ 1213269-23-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 638 - 643
[2] European Journal of Medicinal Chemistry, 2014, vol. 77, p. 75 - 83
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4832 - 4837

[ 76661-24-0 ] Synthesis Path-Downstream 1~88

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).

Reference： [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.

Reference： [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.

Reference： [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.

Reference： [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 ]

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

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

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

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

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

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

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

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

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

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

Reference： [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 ]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Reference： [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 ]

Reference： [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 ]

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

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

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

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

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

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

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

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

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

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

Reference： [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 ]

Reference： [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 ]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

36
[ 76661-24-0 ]
C₂₃H₂₄ClF₃N₆O [ No CAS ]

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

37
[ 76661-24-0 ]
[ 1254783-12-4 ]

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

38
[ 76661-24-0 ]
[ 1254783-30-6 ]

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

39
[ 76661-24-0 ]
[ 1265526-94-0 ]

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

40
[ 76661-24-0 ]
[ 1214265-56-1 ]

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

41
[ 76661-24-0 ]
[ 1213269-23-8 ]

42
[ 76661-24-0 ]
[ 1254783-11-3 ]

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

43
[ 76661-24-0 ]
[ 1254783-18-0 ]

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

44
[ 76661-24-0 ]
[ 1254783-58-8 ]

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

45
[ 76661-24-0 ]
[ 1254783-19-1 ]

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

46
[ 76661-24-0 ]
[ 1254783-20-4 ]

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

47
[ 76661-24-0 ]
[ 1265527-04-5 ]

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

48
[ 76661-24-0 ]
[ 1265527-06-7 ]

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

49
[ 76661-24-0 ]
[ 1265527-08-9 ]

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

50
[ 16153-81-4 ]
[ 76661-24-0 ]
[ 1265527-54-5 ]

Yield	Reaction Conditions	Operation in experiment
71.5%	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.

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

51
[ 76661-24-0 ]
[ 450-91-9 ]
C₁₇H₁₂ClFN₄O₄ [ No CAS ]

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

52
[ 76661-24-0 ]
[ 70261-82-4 ]
C₂₂H₂₃ClN₆O₃ [ No CAS ]

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

53
[ 76661-24-0 ]
[ 103348-14-7 ]
C₂₂H₁₆ClN₅O₄ [ No CAS ]

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

54
[ 554-84-7 ]
[ 5750-76-5 ]
[ 76661-24-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 3h;	To a stirred solution of 77 (20.0 g, 109.0 mmol), in DMF (100.0 mL) wasadded 3-nitrophenol (15.10 g, 109.0 mmol) and K2C03 (16.0 g, 116.0 mmol) and the reaction mixture was heated at 60C for 3h. It was then cooled, ice cooled water (150 mL) was added, precipitation was observed that was filtered through sintered funnel. Filter cake was washed with ether (50 mL) and concentrated under reduced pressure. The residue obtained was further purified via column chromatography (Si02, 100- 200 mesh,10% EtOAc-hexane) to obtain 2,5-dichloro-4-(3-nitrophenoxy)pyrimidine 116 (27 g,87% yield) as white solid. 1HNMR (400 MHz, DMSO): 9.88 (s, 1H), 8.29 (t, 1H), 8.23(dd, 1H), 8.02 (dd, 1H), 7.68 (t, 1H).
87%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2h;	Potassium carbonate (2.26 g, 16.4 mmol) and <strong>[5750-76-5]2,4,5-trichloropyrimidine</strong> (1.5 g, 8.19 mmol) were added to a solution of 3-nitrophenol (1.2 g, 8.19 mmol) in N,N-dimethylformamide (20 mL). The reaction mixture was heated to 60 C. for 2 hours and after cooling was filtered and the filtrate was dilute with ethyl acetate (3*500 mL) and washed with water (20 mL) three times. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo to afford 2.0 g (yield 87%) of a light yellow solid. 1H NMR 400 MHz (DMSO-d6) delta 8.88 (s, 1H), 8.30 (d, J=2 Hz, 1H), 8.29-8.21 (m, 1H), 7.85-7.81 (m, 2H); LCMS m/e: 286 [M]+.
86%	With potassium carbonate; In N,N-dimethyl-formamide; for 2h;Heating;	Potassium carbonate (0.75 g, 5.45 mmol) and <strong>[5750-76-5]2,4,5-trichloropyrimidine</strong>(0.50 g, 2.72 mmol) were added to a solution of 3-nitrophenol(0.38 g, 2.72 mmol) in DMF (10 mL). The reaction washeated to 60 C and stirred for 2 h. Then it was cooled to ambienttemperature and filtered through celite. The filtrate was dilutedwith ethyl acetate (20 mL) and washed with 1 M HCl (20 mL),water (10 mL) and brine (10 mL). The organic layer was dried overanhydrous sodium sulfate and concentrated to afford 0.67 g of titlecompound 8 (2.34 mmol, 86%) as light yellow solid. The productwas used without further purification.

78%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 2h;	General procedure: To a solution of ortho, meta or para nitrophenol (1.21 g, 8.72 mmol) in DMF (20 mL) was added potassium carbonate (2.42 g, 17.5 mmol) and <strong>[5750-76-5]2,4,5-trichloropyrimidine</strong> (1.0 mL, 8.72 mmol). The mixture was heated at 90 C with stirring for 2 h until the reaction was completed. The reaction mixture was filtered, the filtrate was diluted with ethyl acetate (30 mL) and washed three times with water (3 x 20 mL). The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated to afford a light yellow solid. The crude product was then purified by flash silica gel chromatography using hexane and ethyl acetate (7:3) to obtain the desired products in yields ranging from 78 - 83%.
280 g	With potassium carbonate; In N,N-dimethyl-formamide; at 27 - 50℃; for 3h;	The control temperature is 27 C lower, will 198g type 1 illustrated compound 2, 4, 5-trichloro pyrimidine containing to 300g of potash 750mlDMF in the solvent, then adding 150g type 2 compound 3-nitro phenol, then the control temperature is 50 C, reaction 3 hours. TLC in the reaction process (PE:EA=10:1) monitoring after the reaction is complete, the reaction solution is poured into the 15 times in volume of water, drying the concentrated precipitate takes organizing compound layer solid; then filtering, the filter cake is washed with methanol after washing eluviation drying, by preparing 280g formula 3 illustrated compound 2,5-dichloro-4 - (3-nitrophenoxy) pyrimidine.
	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2h;Inert atmosphere;	Will be a meta-nitro phenol (5 g, 35.9 mmol) dissolved in N, N - dimethyl formamide (80 ml) in, adding potassium carbonate (9.9 g, 71.8 mmol), the reaction bottle slowly dropping in the 2, 4, 5 - trichloro pyrimidine (1 A) (6.6 g, 35.9 mmol), 60 C reaction 2 hours. After the reaction, cooling to room temperature, adding ethyl acetate (80 ml), washed with water (80 ml × 3), saturated salt water washing (80 ml × 1), anhydrous sodium sulfate drying, filtering, the filtrate is concentrated under reduced pressure to get the yellow solid of 2, 5 - dichloro -4 - (3 - nitrophenoxy) pyrimidine (1 B) the crude product (9.5 g, yield 92.2%), without further purification directly used for the next step reaction.

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 4738 - 4748
[2]Patent: WO2015/25197,2015,A1 .Location in patent: Paragraph 000204
[3]Patent: US2018/208564,2018,A1 .Location in patent: Paragraph 0379-0380
[4]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 2767 - 2780
[5]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4832 - 4837
[6]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 638 - 643
[7]Patent: WO2013/169401,2013,A1 .Location in patent: Page/Page column 48
[8]European Journal of Medicinal Chemistry,2014,vol. 77,p. 75 - 83
[9]Patent: CN105777652,2016,A .Location in patent: Paragraph 0025; 0026
[10]Patent: CN106916112,2017,A .Location in patent: Paragraph 0038; 0060; 0061; 0062; 0063; 0064; 0065

55
[ 76661-24-0 ]
[ 1374641-74-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With iron; ammonium chloride; In tetrahydrofuran; water; at 65℃; for 3.0h;	Intermediate 1-4 (0.48 g, 1.68 mmol) was dissolved in a solution of THF (50 ml) and water (50 ml). Iron powder (0.47g, 8.4mmol) and ammonium chloride (0.45g, 8.4mmol) were added, and the reaction solution was heated to 65C and stirred for 3 hours. After the reaction mixture was cooled, it was filtered through Celite. After the reaction solution was concentrated in vacuo, it was neutralized with sodium carbonate, and extracted three times with EA (20 ml). The organic layer was separated, dried with anhydrous sodium sulfate, concentrated, and column chromatography to obtain product 1-5b with a yield of 78%.

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 4738 - 4748
[2]Patent: CN111393377,2020,A .Location in patent: Paragraph 0071; 0099-0103

56
[ 76661-24-0 ]
[ 1374641-75-4 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 4738 - 4748
[2]Patent: CN111393377,2020,A

57
[ 76661-24-0 ]
[ 1436851-28-3 ]

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58
[ 76661-24-0 ]
[ 1436851-29-4 ]

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59
[ 76661-24-0 ]
[ 1436851-31-8 ]

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60
[ 76661-24-0 ]
[ 1436851-32-9 ]

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61
[ 76661-24-0 ]
[ 1436851-33-0 ]

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62
[ 76661-24-0 ]
[ 1436851-34-1 ]

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63
[ 76661-24-0 ]
[ 1436851-35-2 ]

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64
[ 76661-24-0 ]
[ 1436851-36-3 ]

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65
[ 76661-24-0 ]
[ 1436851-37-4 ]

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66
[ 76661-24-0 ]
[ 1436851-38-5 ]

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67
[ 76661-24-0 ]
[ 1436851-39-6 ]

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68
[ 76661-24-0 ]
[ 1436851-40-9 ]

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69
[ 76661-24-0 ]
[ 1436851-41-0 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 4738 - 4748

70
[ 76661-24-0 ]
C₁₂H₁₉N₂O₂P [ No CAS ]
C₂₂H₂₃ClN₅O₅P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89 mg	With trifluoroacetic acid; In iso-butanol; at 100℃;	IM4 was prepared according to a literature procedure {Nature 2009, 462, 1070). This material (400 mg) underwent a SNAr reaction with IM3 (308 mg) under standard condition (TFA, 2-BuOH, 100 C, overnight). Conventional workup followed by flash chromatography on silica gel (eluent: 0-15% MeOH in DCM) afforded IM5 as a white foam (89 mg, 15%).

Reference： [1]Patent: WO2013/169401,2013,A1 .Location in patent: Page/Page column 96-97

71
[ 76661-24-0 ]
[ 1407520-10-8 ]

Reference： [1]Patent: WO2013/169401,2013,A1

72
[ 76661-24-0 ]
[ 1407519-19-0 ]

Reference： [1]Patent: WO2013/169401,2013,A1

73
[ 76661-24-0 ]
[ 1197956-03-8 ]
[ 1407520-09-5 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 120.0℃;Sealed tube;	Compound 19 (154mg, 0.54mmol) and compound 20 (107mg, 0.54mmol) were dissolved in 4 mL anhydrous DMF in a sealed tube and was added Pd(OAc)2 (14mg, 0.062mmol), XantPhos (37mg, 0.064mmol), and K3PO4 (150mg, 0.71 mmol). The content was heated at 120 C overnight. After cooling to the room temp, EtOAc was added and the mixture was filtered through celite, washed with more EtOAc. Combined filtrate was cone in vacuo, and the residue was purified by CombiFlash (MeOH/DCM). The product 21 (140 mg, yield 58%) was obtained as an orange solid.

Reference： [1]Patent: WO2013/169401,2013,A1 .Location in patent: Page/Page column 48-49

74
[ 76661-24-0 ]
[ 1588522-80-8 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 77,p. 75 - 83

75
[ 76661-24-0 ]
[ 1588522-82-0 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 77,p. 75 - 83

76
[ 76661-24-0 ]
[ 1588522-84-2 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 77,p. 75 - 83

77
[ 76661-24-0 ]
[ 1588522-86-4 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 77,p. 75 - 83

78
[ 76661-24-0 ]
[ 1588522-88-6 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 77,p. 75 - 83

79
[ 1201935-36-5 ]
[ 76661-24-0 ]
5-chloro-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-4-(3-nitrophenoxy)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With trifluoroacetic acid; In iso-butanol; at 100℃; for 16h;Inert atmosphere;	To a solution of 2,5-dichloro-4-(3-nitrophenoxy)pyrimidine 116 (0.50 g, 1.76 mmol) in 2-butanol (20 mL) and was added 1-(1-methylpiperidin-4-yl)-IH-pyrazol-4- amine precursor-03 (0.35 g, 1.93 mmol) and trifluoroacetic acid (0.22 g, 1.93 mmol) and the reaction mixture was heated at 100C for 16 h under N2 atmosphere. After the completion of reaction (TLC monitored), reaction mixture was basified with saturated aqueous NaHCO3 solution (50 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic layer was washed with brine (50 mL), dried over Na2SO4 andconcentrated under reduced pressure. The residue obtained was purified through column chromatography (Si02, 60-120 mesh, 10% MeOH-DCM) to obtain 5-chloro-N-(1-(1- methylpiperidin-4-yl)- 1 H-pyrazol-4-yl)-4-(3 -nitrophenoxy)pyrimidin-2-amine 117 (0.5 g, 66% yield) as yellow solid. MS: 430.03 (M+H).

Reference： [1]Patent: WO2015/25197,2015,A1 .Location in patent: Paragraph 000205

80
[ 76661-24-0 ]
N-(3-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 2767 - 2780
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4832 - 4837

81
[ 76661-24-0 ]
8-(4-amino-3-methoxyphenyl)-8-azabicyclo[3.2.1]octan-3-ol [ No CAS ]
C₂₄H₂₄ClN₅O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With trifluoroacetic acid; In iso-butanol; at 100℃;	A mixture of intermediate 1 (286 mg, 1 mmol)And Intermediate 7 (249 mg, 1 mmol)Was dissolved in sec-butanol (8 ml)To a solution of 74 mg of trifluoroacetic acid,100 reaction monitored by TLC until the starting material the reaction is complete,After cooling to room temperature,The solution was neutralized by addition of saturated sodium bicarbonate,Ethyl acetate (50 ml * 3)And washed with a saturated sodium chloride solution (100 ml * 2)The resulting organic phase was dried over anhydrous sodium sulfate,The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give Compound 9 (216 mg, yellow solid) in a yield of 43%.

Reference： [1]Patent: CN105601631,2016,A .Location in patent: Paragraph 0027; 0032; 0033

82
[ 76661-24-0 ]
3-fluoro-2-methoxy-4-(4-methylpiperazin-1-yl)aniline [ No CAS ]
5-chloro-N-[3-fluoro-2-methoxy-4-(4-methylpiperazin-1-yl)phenyl]-4-(3-nitrophenoxy)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.7 g	With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 120℃; for 2.0h;Inert atmosphere;	The 2, 5 - dichloro -4 - (3 - nitrophenoxy) pyrimidine (1 B) (0.5 g, 1.7 mmol) and 3 - fluoro -2 - methoxy -4 - (4 - methyl piperazine -1 - yl) aniline (1 E) (0.487 g, 2 . 04 mmol) dissolved in N, N - dimethyl formamide (10 ml) in, to join the toluene sulfonic acid (0.439 g, 2 . 55 mmol), 120 C reaction 2 hours. After the reaction, cooling to room temperature, the addition of water (30 ml), dichloromethane is used for extraction (30 ml × 1), washed with water (30 ml × 1), saturated salt is washed with water (30 ml × 1), anhydrous sodium sulfate drying, filtering, the filtrate is concentrated under reduced pressure, the residue separation and purification with silica gel column chromatography (dichloromethane/methanol=(v/v) 100/1 - 15/1), get the yellow solid of 5 - chloro - N - (3 - fluoro -2 - methoxy -4 - (4 - methyl piperazine -1 - yl) phenyl) -4 - (3 - nitrophenoxy) pyrimidine -2 - amine (1 F) (0.7 g, yield 84.33%).

Reference： [1]Patent: CN106916112,2017,A .Location in patent: Paragraph 0038; 0060; 0078; 0079; 0080; 0081; 0082; 0083

83
[ 76661-24-0 ]
N-(3-((5-chloro-2-((2-methoxy-4-(4-(methyl-d3)piperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)acrylamide [ No CAS ]

Reference： [1]Patent: CN111393377,2020,A
[2]Patent: CN111393377,2020,A

84
[ 76661-24-0 ]
C₁₂H₁₆⁽²⁾H₃N₃O [ No CAS ]
5-chloro-N-(2-methoxy-4-(4-(methyl-d3)piperazin-1-yl)phenyl)-4-(3-nitrophenoxy)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With trifluoroacetic acid; In tert-butyl alcohol; at 100℃; for 3.0h;	Place Intermediate 1-3 (1.57g, 0.7mmol) and Intermediate 1-4 (1.99g, 0.7mmol), TFA (0.08ml, 1.05mmol), and 2-tert-butanol (30ml) in the reaction flask , Heat to 100C and maintain for 3 hours. The reaction solution was cooled to room temperature, saturated sodium carbonate was neutralized, and the aqueous phase was extracted three times with dichloromethane (20 ml). Purified by column chromatography to obtain product 1-5a with a yield of 74%.

Reference： [1]Patent: CN111393377,2020,A .Location in patent: Paragraph 0071; 0074; 0087-0089

85
[ 76661-24-0 ]
[ 7474-82-0 ]
N1-(5-chloro-4-(3-nitrophenoxy)pyrimidin-2-yl)-2-methoxy-N4,N4-dimethylbenzene-1,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.8%	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. 4.1.4.1. N1-(5-chloro-4-(3-nitrophenoxy)pyrimidin-2-yl)-2-methoxy-N4,N4-dimethylbenzene-1,4-diamine (7a). To a solution of 3a and 6ain 2-BuOH were added TFA. Orange solid, 69.8% yield; 1H NMR(500 MHz, DMSO-d6) d 8.35 (s, 1H), 8.30 (s, 1H), 8.17e8.14 (m, 2H),7.75e7.73 (m, 2H), 7.01 (s, 1H), 6.24 (s, 1H), 5.95 (s, 1H), 3.69 (s, 3H),2.83 (s, 6H).

Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 210

86
[ 76661-24-0 ]
[ 2165-85-7 ]
N1-(5-chloro-4-(3-nitrophenoxy)pyrimidin-2-yl)-N4,N4-diethyl-2-methoxybenzene-1,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.3%	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.

Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 210

87
[ 76661-24-0 ]
3-methoxy-N1,N1-dipropylbenzene-1,4-diamine [ No CAS ]
N1-(5-chloro-4-(3-nitrophenoxy)pyrimidin-2-yl)-2-methoxy-N4,N4-dipropylbenzene-1,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52.7%	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.

Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 210

88
[ 143525-62-6 ]
[ 76661-24-0 ]
5-chloro-N-(2-methoxy-4-(pyrrolidin-1-yl)phenyl)-4-(3-nitrophenoxy)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.8%	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.

Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 210

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
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P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
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P312	Call a POISON CENTER or doctor/physician if you feel unwell.
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P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
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P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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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. 76661-24-0 ] {[proInfo.proName]}

Quality Control of [ 76661-24-0 ]

Related Doc. of [ 76661-24-0 ]

Product Details of [ 76661-24-0 ]

Calculated chemistry of [ 76661-24-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 76661-24-0 ]

Application In Synthesis of [ 76661-24-0 ]

[ 76661-24-0 ] Synthesis Path-Upstream 1~1

[ 76661-24-0 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 76661-24-0 ]

Aryls

Chlorides

Ethers

Nitroes

Related Parent Nucleus of [ 76661-24-0 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 76661-24-0 ]

Related Parent Nucleus of
[ 76661-24-0 ]