[ CAS No. 99-55-8 ]

Name: 99-55-8|2-Methyl-5-nitroaniline|98%
Brand: Ambeed
SKU: A401040
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Quality Control of [ 99-55-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 99-55-8 ]

CAS No. :	99-55-8	MDL No. :	MFCD00007741
Formula :	C₇H₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	152.15 g/mol	Pubchem ID :	7444
Synonyms :

Safety of [ 99-55-8 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P273-P280-P301+P310-P311	UN#:	2660
Hazard Statements:	H301+H311+H331-H351-H412	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 99-55-8 ]

Upstream synthesis route of [ 99-55-8 ]
Downstream synthetic route of [ 99-55-8 ]

[ 99-55-8 ] Synthesis Path-Upstream 1~24

1
[ 99-55-8 ]
[ 23244-88-4 ]

Reference： [1] Chemische Berichte, 1890, vol. 23, p. 3642[2] Chemische Berichte, 1892, vol. 25, p. 3152
[3] Chemische Berichte, 1890, vol. 23, p. 3642[4] Chemische Berichte, 1892, vol. 25, p. 3152

2
[ 99-55-8 ]
[ 6967-12-0 ]

3
[ 99-55-8 ]
[ 7597-18-4 ]

Reference： [1] Patent: US3988347, 1976, A,
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2339 - 2352
[3] European Journal of Medicinal Chemistry, 1986, vol. 21, # 4, p. 359 - 362
[4] Chemische Berichte, 1904, vol. 37, p. 2583
[5] Chemische Berichte, 1890, vol. 23, p. 3642[6] Chemische Berichte, 1892, vol. 25, p. 3152
[7] Chemische Berichte, 1893, vol. 26, p. 2352
[8] Chemische Berichte, 1920, vol. 53, p. 1213,1216, 1227
[9] Diss. <Braunschweig 1930>, S. 39,
[10] Chinese Chemical Letters, 2014, vol. 25, # 7, p. 989 - 994
[11] Patent: CN103739550, 2016, B, . Location in patent: Paragraph 0229-0232

4
[ 99-55-8 ]
[ 5428-54-6 ]
[ 7597-18-4 ]

Reference： [1] Chemische Berichte, 1890, vol. 23, p. 3642[2] Chemische Berichte, 1892, vol. 25, p. 3152
[3] Chemische Berichte, 1884, vol. 17, p. 265

5
[ 99-55-8 ]
[ 7597-18-4 ]

Reference： [1] Chemische Berichte, 1904, vol. 37, p. 2583

6
[ 64-19-7 ]
[ 7597-18-4 ]
[ 99-55-8 ]

Reference： [1] Chemische Berichte, 1892, vol. 25, p. 3156

7
[ 99-55-8 ]
[ 70315-68-3 ]

8
[ 99-55-8 ]
[ 70315-70-7 ]

Reference： [1] Patent: CN103739550, 2016, B,

9
[ 99-55-8 ]
[ 50593-30-1 ]

Reference： [1] Chinese Chemical Letters, 2014, vol. 25, # 7, p. 989 - 994

10
[ 99-55-8 ]
[ 22952-24-5 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2017, vol. 65, # 35, p. 7661 - 7668

11
[ 2464-33-7 ]
[ 7664-41-7 ]
[ 603-83-8 ]
[ 99-55-8 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1884, vol. 225, p. 385

12
[ 7664-93-9 ]
[ 95-53-4 ]
[ 603-83-8 ]
[ 99-52-5 ]
[ 99-55-8 ]

Reference： [1] Journal of the Chemical Society, 1891, vol. 59, p. 1017

13
[ 121-14-2 ]
[ 95-80-7 ]
[ 95-86-3 ]
[ 119-32-4 ]
[ 99-55-8 ]

Reference： [1] Chemosphere, 2002, vol. 46, # 4, p. 553 - 560

14
[ 99-55-8 ]
[ 7745-91-7 ]

Reference： [1] Chem. Zentralbl., 1910, vol. 81, # I, p. 260

15
[ 99-55-8 ]
[ 5428-54-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 11, p. 2867 - 2879
[2] Tetrahedron Letters, 1996, vol. 37, # 44, p. 7947 - 7950
[3] Chemische Berichte, 1905, vol. 38, p. 3792
[4] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 3374 - 3379[5] Zhurnal Obshchei Khimii, 1960, vol. 30, # 10, p. 3407 - 3412
[6] Chemische Berichte, 1984, vol. 117, # 6, p. 2275 - 2286
[7] Patent: US5134144, 1992, A,

16
[ 121-14-2 ]
[ 5428-54-6 ]
[ 119-32-4 ]
[ 99-55-8 ]

Reference： [1] Russian Chemical Bulletin, 2009, vol. 58, # 10, p. 2070 - 2076

17
[ 99-55-8 ]
[ 5428-54-6 ]
[ 7597-18-4 ]

Reference： [1] Chemische Berichte, 1890, vol. 23, p. 3642[2] Chemische Berichte, 1892, vol. 25, p. 3152
[3] Chemische Berichte, 1884, vol. 17, p. 265

18
[ 99-55-8 ]
[ 99-60-5 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1907, vol. 355, p. 366[2] Justus Liebigs Annalen der Chemie, 1909, vol. 371, p. 388

19
[ 99-55-8 ]
[ 7745-92-8 ]

Reference： [1] Chemische Berichte, 1897, vol. 30, p. 3000
[2] Chemische Berichte, 1908, vol. 41, p. 2077

20
[ 99-55-8 ]
[ 6269-91-6 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2017, vol. 65, # 35, p. 7661 - 7668

21
[ 99-55-8 ]
[ 2297-06-5 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2017, vol. 65, # 35, p. 7661 - 7668

22
[ 99-55-8 ]
[ 2835-95-2 ]

Reference： [1] Chemische Berichte, 1884, vol. 17, p. 265
[2] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 3374 - 3379[3] Zhurnal Obshchei Khimii, 1960, vol. 30, # 10, p. 3407 - 3412

23
[ 99-55-8 ]
[ 78468-34-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 19, p. 4171 - 4178
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 23, p. 4818 - 4821

24
[ 99-55-8 ]
[ 404844-11-7 ]

Reference： [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 249 - 255
[2] Organic Letters, 2012, vol. 14, # 15, p. 3920 - 3923

[ 99-55-8 ] Synthesis Path-Downstream 1~25

1
[ 99-55-8 ]
[ 7745-92-8 ]

Reference： [1]Chemische Berichte,1897,vol. 30,p. 3000

2
[ 131001-86-0 ]
[ 99-55-8 ]
[ 176915-37-0 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2508 - 2517

3
[ 14418-84-9 ]
[ 99-55-8 ]
[ 374932-28-2 ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 7899 - 7907

4
[ 99-55-8 ]
[ 152460-09-8 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 249 - 255
[2]Patent: WO2011/39782,2011,A1
[3]Patent: WO2011/39782,2011,A1
[4]Organic Process Research and Development,2012,vol. 16,p. 1794 - 1804
[5]Patent: WO2013/35102,2013,A1
[6]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 623 - 632
[7]Dalton Transactions,2014,vol. 43,p. 13299 - 13306
[8]RSC Advances,2016,vol. 6,p. 61458 - 61467
[9]Patent: CN103739550,2016,B
[10]Medicinal Chemistry Research,2019,vol. 28,p. 633 - 645
[11]Patent: CN102796110,2016,B
[12]Patent: CN110078706,2019,A
[13]Drug Design, Development and Therapy,2019,vol. 13,p. 4225 - 4238
[14]Patent: CN111039921,2020,A

5
[ 99-55-8 ]
[ 404844-11-7 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 249 - 255
[2]Organic Letters,2012,vol. 14,p. 3920 - 3923
[3]Patent: CN102796110,2016,B

6
[ 99-55-8 ]
[ 78468-34-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 4171 - 4178
[2]Journal of Medicinal Chemistry,2003,vol. 46,p. 4818 - 4821

7
[ 99-55-8 ]
[ 70315-68-3 ]

Reference： [1]Chemische Berichte,1890,vol. 23,p. 3642
Chemische Berichte,1892,vol. 25,p. 3152
[2]Chemische Berichte,1890,vol. 23,p. 3642
Chemische Berichte,1892,vol. 25,p. 3152

8
[ 99-55-8 ]
[ 23244-88-4 ]

Reference： [1]Chemische Berichte,1890,vol. 23,p. 3642
Chemische Berichte,1892,vol. 25,p. 3152
[2]Chemische Berichte,1890,vol. 23,p. 3642
Chemische Berichte,1892,vol. 25,p. 3152

9
[ 106047-28-3 ]
[ 99-55-8 ]
1-methyl-4-nitro-2-[2-(pyridin-3-yl)pyridin-6-ylamino]benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 110℃; for 24h;	Step 2 1-methyl-4-nitro-2-[2-(3-pyridyl)pyridin-6-ylamino]benzene This compound was prepared by version of the method described in the document (J. Org. Chem., 2000, 65, 1144-1157.). To 940 mg of 2-bromo-6-(3-pyridyl)pyridine obtained in the step 1, 730 mg of 2-methyl-5-nitroaniline, 37 mg of tris(dibenzylideneacetone)dipalladium (0), 75 mg of (+-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl [(+-)-BINAP] and 1.82 mg of cesium carbonate, 12 ml of toluene was added and the mixture was stirred with heating at 110C for 24 hours under an argon atmosphere. After air cooling, the reaction solution was diluted with ethyl acetate and insolubles were removed by filtration. The solvent in the filtrate was distilled off under reduced pressure and the residue was crystallized by adding diethyl ether. The resulting crystal was collected by filtration and then washed with ethyl acetate-diethyl ether to obtain 646 mg of the objective compound as a yellow crystal. Melting point: 148-150C 1H-NMR(CDCl3)delta: 2.42(3H, s), 6.53(1H, br), 6.80(1H, d), 7.35(2H, d), 7.44(1H, dd), 7.69(1H, m), 7.83(1H, dd), 8.44(1H, dt), 8.65(1H, dd), 9.09(1H, d), 9.20(1H, d)

Reference： [1]Patent: EP1533304,2005,A1 .Location in patent: Page/Page column 22; 23

10
[ 99-55-8 ]
[ 483324-01-2 ]
[ 152460-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In butan-1-ol; for 38h;Heating / reflux;	A 250 ml reactor, equipped with a mechanical stirrer and a reflux condenser, was charged with 2-chloro-4-(3-pyridyl)-pyrimidine (0.5 g, 2.6 mmol), 2-amino-4-nitrotoluene (0.5 g, 3.2 mmol), n-butanol (15 ml) and concentrated HCl (5 drops) and the mixture was refluxed for 38 hours. Then, the mixture was cooled, and 6 N NaOH was added to pH 8. The solvent was evaporated under reduced pressure and water (20 ml) was added to the residue, followed by extraction with dichloromethane (2×20 ml). The combined organic phase was concentrated to dryness to give the crude N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-pyrimidine-amine, which was purified by column chromatography to yield a product having 80% purity. The residue was re-slurried twice in methanol (2×2 ml) and in water (3 ml) and dried under reduced pressure
290 g	With copper(l) iodide; 2-(dimethylamino)ethyl methacrylate; potassium carbonate; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere;	190 g of 2-chloro-4-(pyridin-3-yl)pyridine under a nitrogen atmosphere,167 g of 2-methyl-5-nitroaniline, 47 g of cuprous iodide,Anhydrous potassium carbonate 276gAnd 22 g of dimethylaminoethyl methacrylate added to 1,4-dioxane solution 2000 mLMedium, heating at 100 C, reaction for 20 h, TLC detection,The raw material is completely reacted; first under reduced pressure,Evaporate most of the solvent dioxane, after cooling to room temperature,The reaction mixture was poured into ice water and a large amount of white solid precipitated.Filtration, a small amount of n-hexane rinse, vacuum dry to pureN-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidinamine 290 g.

Reference： [1]Patent: US2006/149061,2006,A1 .Location in patent: Page/Page column 8; 9
[2]Patent: CN109305961,2019,A .Location in patent: Paragraph 0041; 0042; 0043

11
[ 34785-11-0 ]
[ 99-55-8 ]
[ 873051-10-6 ]

Yield	Reaction Conditions	Operation in experiment
8%		94; N-(5-Amino-2-methyl-phenyl)-4-oxo-lH-quinoline-3-carboxamide; To a solution of <strong>[34785-11-0]4-hydroxy-quinoline-3-carboxylic acid</strong> (A-1) (50 mg, 0.26 mmol), HBTU (99mg, 0.26 mmol) and DIEA (138 jaL, 0.79 mmol) in THF (2.6 mL) was added 2-methyl-5-nitro-phenylamine (40 mg, 0.26 mmol). The mixture was heated at 150 C in the microwave for 20min and the resulting solution was concentrated. The residue was dissolved in EtOH (2 mL) andSnCl2-2H2O (293 mg, 1.3 mmol) was added. The reaction was stirred at room temperatureovernight. The reaction mixture was basified with sat. NaHCOs solution to pH 7-8 and extractedwith ethyl acetate. The combined organic layers were washed with brine, dried over NaaSO,*,filtered and concentrated. The residue was dissolved in DMSO and purified by HPLC (10-99 %CHsCN / H2O) to yield the product, N-(5-amino-2-methyl-phenyl)-4-oxo-lH-quinoline-3-carboxamide (94) (6 mg, 8 %). HPLC ret. time 2.06 min, 10-99 % CH3CN, 5 min run; ESI-MS294.2 m/z (MH+).

Reference： [1]Patent: WO2006/2421,2006,A2 .Location in patent: Page/Page column 251

12
[ 55496-52-1 ]
[ 99-55-8 ]
(7-methoxy-quinazolin-4-yl)-(2-methyl-5-nitro-phenyl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98.9%	In isopropyl alcohol; for 12.0h;Heating / reflux;	Method 63; (7-Methoxy-quinazolin-4-ylV(2-methyl-5-nitro-phenyl*)-amine; A mixture of <strong>[55496-52-1]4-chloro-7-methoxy-quinazoline</strong> (Method 32; 3.5 g, 18 mmol) and 2- methyl-5-nitro-phenylamine (2.3 g, 15 mmol) in isopropanol (150 ml) was refluxed for 12 h. The reaction mixture was cooled to 25 0C and the resulting precipitate was collected by vacuum filtration. The solid was washed with ether and dried under reduced pressure to give 4.6 g (98.9%) of a light yellow solid. NMR: 11.55 (s, br, IH), 8.85 (s, IH), 8.75 (d, IH), 8.30 (s, IH), 8.20 (d, IH), 7.75 (d, IH), 7.52 (d, IH), 7.30 (s, IH), 4.02 (s, 3H), 2.40 (s, 3H); m/z 310.

Reference： [1]Patent: WO2007/71963,2007,A2 .Location in patent: Page/Page column 58

13
[ 22536-63-6 ]
[ 99-55-8 ]
[ 1025717-15-0 ]

Yield	Reaction Conditions	Operation in experiment
70.6%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; In 1,4-dioxane; water; at 110℃;	To a mixture of <strong>[22536-63-6]<strong>[22536-63-6]2-chloro-4-methoxypyrimidin</strong>e</strong> (9.54 g, 66 mmol), 2-methyl-5- nitrobenzenamine (10.0 g, 66 mmol), Pd2(dba)3 (1.0 g), S-Phos (1.0 g, 24.4 mmol), and Cs2C03 (31.8 g, 99 mmol) in 1,4-dioxane/water (140 mL/60 mL) was heated at 110C overnight. The mixture was cooled to room temperature and then filtered through a pad of celite. The filtrate was diluted with ethyl acetate and washed with water. The organic phase was dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel to afford compound 12 (12 g.70.6% yield) as a light yellow solid.
70.6%	With tris-(dibenzylideneacetone)dipalladium(0); 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl; caesium carbonate; In 1,4-dioxane; water; at 110℃;	To a mixture of <strong>[22536-63-6]<strong>[22536-63-6]2-chloro-4-methoxypyrimidin</strong>e</strong> (9.54 g, 66 mmol), 2-methyl-5- nitrobenzenamine (10.0 g, 66 mmol), Pd2(dba)3 (1.0 g), S-Phos (1.0 g, 24.4 mmol), and Cs2C03 (31.8 g, 99 mmol) in 1,4-dioxane/water (140 mL/60 mL) was heated at 110C overnight. The mixture was cooled to room temperature and then filtered through a pad of celite. The filtrate was diluted with ethyl acetate and washed with water. The organic phase was dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel to afford compound 12 (12 g.70.6% yield) as a light yellow solid.
	With sodium t-butanolate;palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; In 1,4-dioxane; at 150℃; for 0.333333h;Microwave irradiation;	To the mixture of <strong>[22536-63-6]<strong>[22536-63-6]2-chloro-4-methoxypyrimidin</strong>e</strong> 18 (10.0 mmol), 2- methyl-5-nitrobenzenamine (15.0 mmol), Pd(OAc)2 (1 mmol), DPE-Phos (1.5 mmol) and NaO-tBu (20.0 mmol) under nitrogen is added 1,4-dioxane (15 mL). The resulting mixture is heated at 150 0C for 20 min under microwave conditions. The reaction mixture is filtered through a pad of celite and the filtrate is diluted in ethyl acetate (100 ml) and washed with water, dried over NaSO4 and concentrated. The crude product is purified by silica gel column chromatography (ethyl acetate : hexanes = 1 : 4 v/v) to afford 4-methoxy-N-(2- methyl-5-nitrophenyl)pyrimidin-2-amine 19 as a light yellow solid. MS (m/z) (M+l)+: 261.1.

Reference： [1]Patent: WO2016/172528,2016,A1 .Location in patent: Page/Page column 41-42
[2]Patent: WO2018/81251,2018,A1 .Location in patent: Page/Page column 60
[3]Patent: WO2008/58037,2008,A1 .Location in patent: Page/Page column 35; 39

14
[ 400743-82-0 ]
[ 20012-63-9 ]
[ 39643-31-7 ]
[ 728918-72-7 ]
C₈H₇F₄N [ No CAS ]
C₃₃H₂₉IN₅O₄Pol [ No CAS ]
[ 91646-45-6 ]
[ 4273-98-7 ]
[ 2264-92-8 ]
[ 1204-44-0 ]
[ 68817-71-0 ]
[ 369-36-8 ]
[ 37750-29-1 ]
[ 55751-54-7 ]
[ 18595-14-7 ]
[ 52562-19-3 ]
[ 62532-99-4 ]
[ 21627-58-7 ]
[ 73818-73-2 ]
[ 54705-91-8 ]
[ 26286-54-4 ]
[ 177171-13-0 ]
[ 99-55-8 ]
[ 23491-48-7 ]
[ 400750-84-7 ]
C₄₂H₃₇N₈O₄Pol [ No CAS ]
C₄₂H₃₇N₈O₄Pol [ No CAS ]
C₄₃H₄₃N₆O₄Pol [ No CAS ]
C₄₂H₃₉N₆O₄Pol [ No CAS ]
C₄₃H₃₇N₆O₄PolS [ No CAS ]
C₄₀H₃₆N₇O₆Pol [ No CAS ]
C₄₂H₃₉N₆O₆Pol [ No CAS ]
C₃₉H₃₃FN₇O₆Pol [ No CAS ]
C₄₄H₃₉N₆O₅Pol [ No CAS ]
C₄₅H₃₈ClN₆O₄Pol [ No CAS ]
C₄₆H₄₁N₆O₄Pol [ No CAS ]
C₄₃H₄₂N₇O₄Pol [ No CAS ]
C₄₆H₄₁N₆O₅Pol [ No CAS ]
C₄₅H₃₈FN₆O₄Pol [ No CAS ]
C₄₅H₃₈ClN₆O₄Pol [ No CAS ]
C₄₁H₃₅F₄N₆O₄Pol [ No CAS ]
C₄₅H₃₉N₆O₆PolS [ No CAS ]
C₄₅H₃₈ClN₆O₄PolS [ No CAS ]
C₄₄H₄₄N₇O₄Pol [ No CAS ]
C₄₇H₄₁N₆O₅Pol [ No CAS ]
C₄₅H₃₉ClN₇O₄Pol [ No CAS ]
C₄₇H₄₁N₆O₆Pol [ No CAS ]
C₄₅H₄₅N₈O₅Pol [ No CAS ]
C₄₄H₄₄N₉O₆Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In ISOPROPYLAMIDE; at 60℃;Combinatorial reaction / High throughput screening (HTS);	Step 2. Catalytic amination of the solid supported 8-iodo-l-methyl-4,5-dihydro- lH-pyrazolo [4,3-h] quinazoline-3-carboxamide; <n="82"/>Using a 4 niL Argonaut Trident synthesizer cassette, 200 mg (0.11 mmol) of the resin from step 1 above, were charged into separate vials. To each of the reactor vials flushed with argon, finely divided potassium carbonate (0.15 g, 1.1 mmol), palladium acetate [Pd(OAc)2] (2.5mg, 0.011 mmol, 10%), (HK)-BINAP (6.8 mg, 0.011 mmol, 10%) and the corresponding amine (0.22 mmol, 2 equivalents) in degassed (argon) dimethyacetamide (2 mL) were added. The resulting mixture was agitated at 600C for 10 hours on the Argonaut Trident Automated Library Synthesizer (ALS) station. The Trident ALS station was programmed to continuously mechanically agitate the resin at 6O0C while a nitrogen gas "sparge" was incorporated to re-suspend the scarcely soluble potassium carbonate. Nitrogen gas sparging was incorporated once per hour, for a 30 second duration, throughout the 16-hour heating cycle.The resin was drained from the synthesis cocktail and washed using the Argonaut Trident External Agitation Thermal Unit (EATU) synthesis station with DMA (3 x 2 mL, 5 min.). The above catalytic amination cycle was repeated a second time using the previously described procedure.Upon completion of the second amination cycle, the resin was drained from the synthesis cocktail and washed using the Argonaut Trident EATU synthesis station with DMF (1 x 2 mL, 5 min.), with water (1 x 2 mL, 5 min.), with DMF/water (1 : 1) (3 x 2 mL, 5 min.), with DMF (3 x 2 mL, 5 min.), with methanol (3 x 2 mL, 5 min.) and with DCM (3 x 2 mL, 5 min.).

Reference： [1]Patent: WO2008/74788,2008,A1 .Location in patent: Page/Page column 80-81

15
2-(methylsulfonyl)-4-(pyridin-3-yl)pyrimidine [ No CAS ]
[ 99-55-8 ]
[ 152460-09-8 ]

Reference： [1]Monatshefte fur Chemie,2010,vol. 141,p. 907 - 911

16
C₁₇H₁₄N₃O₂PolS [ No CAS ]
[ 99-55-8 ]
[ 152460-09-8 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3920 - 3923

17
[ 5751-20-2 ]
[ 99-55-8 ]
[ 1025717-41-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With hydrogenchloride; In water; at 130 - 160℃; for 1.5h;	2-Methythiopyrimidin-4-one (18.6 g, 0.13 mol) and 2-methyl-5- nitrophenylamine (29.7 g, 0.195 mol) were heated to melt at approximately 130 °C. The reaction is conducted in a sealed system with a vent line to exhaust the methanethiol liberated in the reaction. The methanethiol is absorbed in two caustic scrubbers in series connected to vent line, with an empty trap between the reaction vessel and scrubbers to avoid reverse flow of caustic solution into the reaction vessel. Hydrochloric acid (1 ml, 35percent, 0.01 1 mol) was added and the melt heated at 160 °C for 1.5 h forming a solid. Hot acetone (200 ml) was added at 45-50 °C and the mixture was stirred for 0.5 h. Solid was filtered off and washed with acetone (130 ml) and water (60 ml) yielding 24.5 g (76percent) of 2-(2-methyl-5- nitrophenylamino)pyrimidin-4-one. M.p. 271 -273 °C. 1H NMR (DMSO-Ok): 2.12 (s, 3H), 2.36 (s, 3H), 5.74 (s, 1 H), 7.49 (d J=8.4 Hz, 1 H), 7.86 (dd J=8.4;2.5 Hz, 1 H), 8.34 (br.s, 1 H), 9.04 (d J=2.5 Hz, 1 H), 1 1.13 (br.s, 1 H).

Reference： [1]Patent: WO2013/120852,2013,A1 .Location in patent: Page/Page column 11; 12

18
[ 99-55-8 ]
[ 152459-94-4 ]

Reference： [1]Patent: WO2013/120852,2013,A1

19
[ 1194-21-4 ]
[ 99-55-8 ]
[ 1467739-25-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	at 170℃; for 3h;	6-Amino-4-chloropyrimidin-2(1H)-one (3, 200 mg, 0.84 mmol) and 2-methyl-5-nitroaniline (627 mg, 2.52 mmol) were heated at 170 °C for 3 h. The mixture was then cooled to rt and diethyl ether was added. The mixture was sonicated for 5 min. The suspension was filtered, and the filter cake was dissolved in MeOH and purified by column chromatography (silica gel, dichloromethane/methanol 9:1 v/v) to afford 4 (128 mg, 60percent) as a brown solid.

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 2311 - 2316

20
[ 99-55-8 ]
[ 50593-30-1 ]

Reference： [1]Chinese Chemical Letters,2014,vol. 25,p. 989 - 994

21
[ 13721-01-2 ]
[ 99-55-8 ]
C₁₇H₁₃N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 150℃; for 0.333333h;Microwave irradiation;	To a solution of 4-hydroxy-quinoline-3-carboxylic acid (A-1) (50 mg, 0.26 mmol), HBTU (99 mg, 0.26 mmol) and DIEA (138 muL, 0.79 mmol) in THF (2.6 mL) was added 2-methyl-5-nitro-phenylamine (40 mg, 0.26 mmol). The mixture was heated at 150° C. in the microwave for 20 min and the resulting solution was concentrated. The residue was dissolved in EtOH (2 mL) and SnCl2.2H2O (293 mg, 1.3 mmol) was added. The reaction was stirred at room temperature overnight. The reaction mixture was basified with sat. NaHCO3 solution to pH 7-8 and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was dissolved in DMSO and purified by HPLC (10-99percent CH3CN/H2O) to yield the product, N-(5-amino-2-methyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (94) (6 mg, 8percent). HPLC ret. time 2.06 min, 10-99percent CH3CN, 5 min run; ESI-MS 294.2 m/z (MH+).

Reference： [1]Patent: US2015/231142,2015,A1 .Location in patent: Paragraph 0772

22
[ 155542-33-9 ]
[ 99-55-8 ]
tert-butyl (3R)-3-(tert-butoxycarbonylamino)-4-[(2-methyl-5-nitrophenyl)amino]-4-oxobutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 0 - 60℃;	Following the General Procedure of Description 20, tert-butyl (3 )-3-(tert- butoxycarbonylamino)-4-[(2-methyl-5-nitro-phenyl)amino]-4-oxo-butanoate (22a) was prepared from (2R)-4-tert-butoxy-2-(tert-butoxycarbonylamino)-4-oxo-butanoic acid (commercially available or see Example 5 (Variant B)) (1 16 mg, 0.4 mmol), 2-methyl-5- nitro-aniline (61 mg, 0.4 mmol), HATU (228 mg, 0.6 mmol), and DIPEA (210 uL, 155 mg, 1.2 mmol) in anhydrous DMF (1.5 mL) from 0 C? room temperature to 60 C for overnight. Aqueous work-up and purification by silica gel column chromatography using mixtures of ethyl acetate (EtOAc) and hexane (EtOAc/hexane = 1 :4, v/v? EtOAc/hexane = 1 :3, v/v) yielded 123 mg (73% yield) of the title compound (22a) as a dark yellow oil. Rf. -0.74 (EtOAc/Hxn = 1 :2, v/v). 1H MR (300 MHz, CDC13): delta 8.75 (br. s, 1H), 7.90 (dd, J = 8.1, 2.7 Hz, 1H), 7.49 (d, J = 2.4 Hz, 1H), 7.30 (d, J= 8.7 Hz, 1H), 5.97 (br. d, J= 6.9 Hz, 1H), 4.70-4.55 (m, 1H), 2.95 (dd, J = 17.1, 4.5 Hz, 1H), 2.71 (dd, J= 17.1, 6.6 Hz, 1H), 2.36 (s, 3H), 1.48 (s, 9H), 1.47 (s, 9H) ppm. LC/MS: Rt = 2.741 min; ESI (neg.) mlz = 422.0 (M-H+)".

Reference： [1]Patent: WO2017/24009,2017,A1 .Location in patent: Paragraph 0589; 0732

23
[ 99-55-8 ]
[ 2297-06-5 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2017,vol. 65,p. 7661 - 7668

24
[ 99-55-8 ]
[ 6269-91-6 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2017,vol. 65,p. 7661 - 7668

25
[ 22536-64-7 ]
[ 99-55-8 ]
4-methoxy-6-methyl-N-(2-methyl-5-nitrophenyl)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28.8%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 16h;Inert atmosphere;	To a solution under nitrogen gas of compound 510-CN-I-1 (600 mg , 3.797mmol) in 1,4-dioxane (15 ml), compound-3 (578 mg, 3.797mmol) and cesium carbonate (2.148 g, 6.592 mmol) were added. The resulting mixture was degassed 30 min with Argon gas, then Xantphos (440 mg, 0.759 mmol) and Pd2(dba) 3 (348 mg, 0.379 mmol) were added and the reaction mixture was stirred at 100C for 16 h. The reaction mixture was then cooled to room temperature, filtered and concentrated under reduced pressure. The residue was partitioned between brine and AcOEt and the aqueous layer was extracted with AcOEt. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a brown oil. The crude compound was purified by flash chromatography using (silica-gel: 100-200 mesh, AcOEt - petroleum ether; 70%) to give 0.3 g (yield 28.8%) of a pale yellow solid corresponding to 4- methoxy-6-methyl-N-(2-methyl-5-nitrophenyl)pyrimidin-2-amine. Mass: (ES+) C13H14N4O3 required 274.11; found 275.1 [M+H], HPLC/MS method 8.

Reference： [1]Patent: WO2017/191599,2017,A1 .Location in patent: Page/Page column 177

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[ CAS No. 99-55-8 ]

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[ 99-55-8 ] Synthesis Path-Upstream 1~24

[ 99-55-8 ] Synthesis Path-Downstream 1~25

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