[ CAS No. 4923-01-7 ] {[proInfo.proName]}

Name: 4923-01-7|5-Methyl-4H-1,2,4-triazol-3-amine|98%
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Product Details of [ 4923-01-7 ]

CAS No. :	4923-01-7	MDL No. :	MFCD00498236
Formula :	C₃H₆N₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FJRZOOICEHBAED-UHFFFAOYSA-N
M.W :	98.11	Pubchem ID :	234610
Synonyms :

Safety of [ 4923-01-7 ]

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

Application In Synthesis of [ 4923-01-7 ]

* 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 [ 4923-01-7 ]
Downstream synthetic route of [ 4923-01-7 ]

[ 4923-01-7 ] Synthesis Path-Upstream 1~1

1
[ 80772-99-2 ]
[ 2075-46-9 ]
[ 4923-01-7 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1989, vol. 25, # 2, p. 235[2] Khimiya Geterotsiklicheskikh Soedinenii, 1989, # 2, p. 278

[ 4923-01-7 ] Synthesis Path-Downstream 1~85

1
[ 120-57-0 ]
[ 4923-01-7 ]
(5-methyl-1H-[1,2,4]triazol-3-yl)-piperonyliden-amine [ No CAS ]

Reference： [1]Chemische Berichte,1910,vol. 43,p. 1315

2
[ 141-97-9 ]
[ 4923-01-7 ]
[ 89852-99-3 ]

Reference： [1]Chemische Berichte,1910,vol. 43,p. 377
[2]Molecules,2012,vol. 17,p. 8285 - 8302
[3]Chemical Biology and Drug Design,2015,vol. 86,p. 969 - 978
[4]Russian Journal of Bioorganic Chemistry,2017,vol. 43,p. 421 - 428
Bioorg. Khim.,2017,vol. 43,p. 402 - 410,9

3
[ 94-02-0 ]
[ 4923-01-7 ]
2-methyl-5-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one [ No CAS ]

Reference： [1]Chemische Berichte,1910,vol. 43,p. 377

4
[ 123-51-3 ]
[ 103-72-0 ]
[ 4923-01-7 ]
[ 21732-02-5 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1928,vol. 467,p. 277,284

5
[ 103-72-0 ]
[ 4923-01-7 ]
3-amino-5-methyl-[1,2,4]triazole-1-carbothioic acid anilide [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1928,vol. 467,p. 277,284

6
[ 3002-24-2 ]
[ 4923-01-7 ]
[ 90942-52-2 ]

Reference： [1]Chemische Berichte,1910,vol. 43,p. 377

7
[ 123-51-3 ]
[ 4923-01-7 ]
N-allyl-N'-(5-methyl-1H-[1,2,4]triazol-3-yl)-thiourea [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1928,vol. 467,p. 277,284

8
[ 4923-01-7 ]
[ 607-97-6 ]
6-ethyl-2,5-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one [ No CAS ]

Reference： [1]Chemische Berichte,1910,vol. 43,p. 377

9
[ 4923-01-7 ]
[ 123-54-6 ]
[ 7637-33-4 ]

Reference： [1]Chemische Berichte,1910,vol. 43,p. 377

10
[ 4923-01-7 ]
[ 93-91-4 ]
[ 144730-23-4 ]

Reference： [1]Chemische Berichte,1910,vol. 43,p. 377

11
[ 4923-01-7 ]
[ 57-06-7 ]
N-allyl-N'-(5-methyl-1H-[1,2,4]triazol-3-yl)-thiourea [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1928,vol. 467,p. 277,284

12
[ 4923-01-7 ]
[ 15285-15-1 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1898,vol. 303,p. 54

13
[ 4923-01-7 ]
[ 74999-17-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1898,vol. 303,p. 54

14
[ 4923-01-7 ]
[ 41463-66-5 ]

Reference： [1]Chemische Berichte,1893,vol. 26,p. 2599

15
[ 517-23-7 ]
[ 4923-01-7 ]
[ 74258-82-5 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 927 - 937

16
[ 80772-99-2 ]
[ 2075-46-9 ]
[ 4923-01-7 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1989,vol. 25,p. 235
Khimiya Geterotsiklicheskikh Soedinenii,1989,p. 278

17
[ 80772-99-2 ]
[ 106-49-0 ]
[ 137531-32-9 ]
[ 4923-01-7 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1991,vol. 27,p. 952 - 957
Zhurnal Organicheskoi Khimii,1991,vol. 27,p. 1100 - 1105

18
[ 80772-99-2 ]
[ 104-94-9 ]
[ 4923-01-7 ]
[ 137531-33-0 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1991,vol. 27,p. 952 - 957
Zhurnal Organicheskoi Khimii,1991,vol. 27,p. 1100 - 1105

19
[ 106087-68-7 ]
[ 137811-92-8 ]
[ 4923-01-7 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1991,vol. 27,p. 530 - 533
Khimiya Geterotsiklicheskikh Soedinenii,1991,vol. 27,p. 665 - 668

20
[ 13218-13-8 ]
[ 4923-01-7 ]
[ 99777-29-4 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 576 - 582
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 682 - 688

21
[ 626-35-7 ]
[ 4923-01-7 ]
[ 83809-88-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1980,p. 974 - 978
Khimiya Geterotsiklicheskikh Soedinenii,1980,vol. 16,p. 1283 - 1298

22
[ 626-35-7 ]
[ 4923-01-7 ]
C₅H₃N₆O₃^(1-)*K⁽¹⁺⁾ [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1990,vol. 24,p. 646 - 650
Khimiko-Farmatsevticheskii Zhurnal,1990,vol. 24,p. 41 - 44

23
[ 626-35-7 ]
[ 4923-01-7 ]
7-Methyl-3-nitro-1H-[1,2,4]triazolo[5,1-c][1,2,4]triazin-4-one; compound with ammonia [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1990,vol. 24,p. 646 - 650
Khimiko-Farmatsevticheskii Zhurnal,1990,vol. 24,p. 41 - 44

24
[ 603-67-8 ]
[ 4923-01-7 ]
[ 76434-86-1 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1986,vol. 22,p. 543 - 546
Khimiya Geterotsiklicheskikh Soedinenii,1986,vol. 22,p. 662 - 665

25
[ 4428-98-2 ]
[ 4923-01-7 ]
[ 28610-00-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 1121 - 1123

26
[ 34461-00-2 ]
[ 4923-01-7 ]
[ 107753-07-1 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1986,vol. 22,p. 543 - 546
Khimiya Geterotsiklicheskikh Soedinenii,1986,vol. 22,p. 662 - 665

27
[ 4923-01-7 ]
[ 79-22-1 ]
5-Amino-3-methyl-[1,2,4]triazole-1-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1983,vol. 66,p. 694 - 700

28
[ 4923-01-7 ]
[ 51254-62-7 ]
[ 106087-62-1 ]

Reference： [1]Pharmaceutical Chemistry Journal,1986,vol. 20,p. 113 - 117
Khimiko-Farmatsevticheskii Zhurnal,1986,vol. 20,p. 178 - 182

29
[ 4923-01-7 ]
[ 79-44-7 ]
5-Amino-3-methyl-[1,2,4]triazole-1-carboxylic acid dimethylamide [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1983,vol. 66,p. 694 - 700

30
[ 4923-01-7 ]
[ 34461-00-2 ]
[ 80772-99-2 ]

Reference： [1]Pharmaceutical Chemistry Journal,1990,vol. 24,p. 52 - 54
Khimiko-Farmatsevticheskii Zhurnal,1990,vol. 24,p. 39 - 40
[2]Pharmaceutical Chemistry Journal,1986,vol. 20,p. 550 - 554
Khimiko-Farmatsevticheskii Zhurnal,1986,vol. 20,p. 947 - 952

31
[ 4923-01-7 ]
[ 34461-00-2 ]
[ 107753-07-1 ]

Reference： [1]Pharmaceutical Chemistry Journal,1990,vol. 24,p. 52 - 54
Khimiko-Farmatsevticheskii Zhurnal,1990,vol. 24,p. 39 - 40

32
[ 80772-99-2 ]
[ 106-40-1 ]
[ 4923-01-7 ]
[ 123767-92-0 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1991,vol. 27,p. 952 - 957
Zhurnal Organicheskoi Khimii,1991,vol. 27,p. 1100 - 1105

33
[ 44397-85-5 ]
[ 4923-01-7 ]
sodium salt of 2-methyl-6-nitro-7-hydroxy-4,7-dihydro-1,2,4-triazolo<5,1-c><1,2,4>triazine [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1994,vol. 30,p. 47 - 51
Khimiya Geterotsiklicheskikh Soedinenii,1994,p. 52 - 57

34
[ 4923-01-7 ]
[ 24156-65-8 ]

Reference： [1]Russian Journal of Organic Chemistry,1997,vol. 33,p. 1125 - 1132
[2]Russian Journal of Organic Chemistry,1997,vol. 33,p. 1803 - 1804

36
[ 4414-88-4 ]
[ 4923-01-7 ]
(1H-benzoimidazol-2-yl)-[(5-methyl-2H-[1,2,4]triazol-3-yl)-hydrazono]-acetonitrile [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,1999,vol. 35,p. 1355 - 1362

37
[ 4923-01-7 ]
[ 105-53-3 ]
[ 57351-72-1 ]

Reference： [1]Russian Journal of Organic Chemistry,1999,vol. 35,p. 1355 - 1362

38
[ 5841-70-3 ]
[ 4923-01-7 ]
[(5-methyl-2H-[1,2,4]triazol-3-yl)-hydrazono]-phenyl-acetonitrile [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2002,vol. 51,p. 1737 - 1743

39
[ 4923-01-7 ]
formyl[3,5-bis(trifluoroacetyl)phenyl]acetonitrile [ No CAS ]
3-(3,5-bis-trifluoromethyl-phenyl)-7-methyl-[1,2,4]triazolo[5,1-c][1,2,4]triazin-4-ylamine [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2002,vol. 51,p. 1737 - 1743

40
[ 4923-01-7 ]
Lithium; (Z)-1,1,1-trifluoro-4-oxo-4-phenyl-but-2-en-2-olate [ No CAS ]
2-methyl-5-phenyl-7-trifluoromethyl-1,2,4-triazolo[1,5-a]pyrimidine [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2003,vol. 52,p. 1190 - 1194

41
[ 504-02-9 ]
[ 4637-24-5 ]
[ 4923-01-7 ]
2-methyl-8,9-dihydro[1,2,4]triazolo[1,5-a]quinazolin-6(7H)-one [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2005,vol. 54,p. 2903 - 2904

42
[ 126-81-8 ]
[ 4637-24-5 ]
[ 4923-01-7 ]
2,8,8-trimethyl-8,9-dihydro[1,2,4]triazolo[1,5-a]quinazolin-6(7H)-one [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2005,vol. 54,p. 2903 - 2904

43
[ 4923-01-7 ]
[ 25007-54-9 ]
[ 115761-40-5 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; acetic acid;	The (6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[[5-(hydroxycarbamoyl)-2-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid used as the starting material can be prepared as follows: 3-Amino-5-methyl-1H-s-triazole (112 mg) and 320 mg of dimethyl 2-oxo-succinate are dissolved in 5 ml of glacial acetic acid. After boiling under reflux for 22 hours the solvent is distilled off in a vacuum. The residue is suspended in warm methanol. After cooling the product is filtered off and washed several times with methanol. After drying in a high vacuum there are obtained 73 mg of methyl 7-hydroxy-2-methyl-s-triazolo[1,5-a]pyrimidine-5-carboxylate as a beige powder, m.p.>220 C. 1 H NMR (DMSOd6): signals at, inter alia, δ2.44 (s, 3H), 3.88 (s, 3H), 6.54 (s, 1H).
	In methanol; acetic acid;	The (6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[[5-(hydroxycarbamoyl)-2-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid used as the starting compound can be prepared as follows: 3-Amino-5-methyl-1H-s-triazole (112 mg) and 320 mg of dimethyl 2-oxo-succinate are dissolved in 5 ml of glacial acetic acid. After boiling under reflux for 22 hours the solvent is distilled off in a vacuum. The residue is suspended in warm methanol. After cooling the product is filtered off and washed several times with methanol. After drying in a high vacuum there are obtained 73 mg of methyl 7-hydroxy-2-methyl-s-triazolo[1,5-a]pyrimidine-5-carboxylate as a beige powder, m.p.>220 C. 1 H NMR (DMSO-d6): signals at, inter alia, δ2.44 (s, 3H), 3.88 (s, 3H), 6.54 (s, 1H).

Reference： [1]Patent: US5438052,1995,A
[2]Patent: US5438052,1995,A

44
[ 4923-01-7 ]
[ 5457-44-3 ]
[ 150192-09-9 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane	55 Manufacture of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]acetamido]-3-[[[5-[2-(hydroxycarbamoyl)ethyl]-2-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid The (6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[[5-[2-(hydroxycarbamoyl)ethyl]-2-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid used as the starting material can be prepared as follows: 3-Amino-5-methyl-1H-s-triazole (19.8 g) (about 0.12 mol) (about 70%) and 30 g (0.16 mol) of dimethyl 3-oxo-adipate are melted together while gassing with argon for 1 hour in a bath heated at 160° C. In so doing, the volatile products are removed in a water-jet vacuum. After cooling the solid residue is dissolved in dichloromethane/methanol (1:1 v/v). The turbid yellowish solution is filtered and concentrated. The crystals which thereby result are filtered off under suction and washed with ethanol, subsequently with diethyl ether. There are obtained 20 g of methyl 4,7-dihydro-2-methyl-7-oxo-s-triazolo[1,5-a]pyrimidine-5-propionate as a white crystals of melting point 222°-225° C.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US5438052, 1995, A

45
[ 4923-01-7 ]
[ 35144-22-0 ]
[ 41511-69-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; acetonitrile;	EXAMPLE (II-2) STR716 A mixture of 11.2 g (0.06 mol) of 4,6-dimethyl-2-methylsulphonyl-pyrimidine, 5.9 g (0.06 mol) of 3-amino-5-methyl-1,2,4-triazole, 8.3 g (0.06 mol) of potassium carbonate and 100 ml of acetonitrile is boiled to reflux for 5 hours. After evaporating, the residue is stirred into 100 ml of water, the product, which in this process is obtained in the form of crystals, is isolated by filtering off with suction, washed with water and recrystallized from acetonitrile. 4.6 g (37% of theory) of 1-(4,6-dimethylpyrimidin-2-yl)-5-amino-3-methyl-1,2,4-triazole of melting point 237 C. are obtained.

Reference： [1]Patent: US4941912,1990,A

46
[ 4923-01-7 ]
[ 55314-16-4 ]
2-Methyl-7-(pyridin-3-yl)[1,2,4]triazolo[1,5-a]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetic acid;	EXAMPLE 5 2-Methyl-7-(3-pyridyl)[1,2,4]triazolo[1,5-a]pyrimidine A reaction mixture of 0.98 g of 3-amino-5-methyl-1,2,4-triazole and 1.76 g of 3-dimethylamino-1-(3-pyridyl)-2-propene-1-one in 25 ml of glacial acetic acid was refluxed for six hours. The procedure was continued as for Example 1 to give 0.85 g of the product of the Example as colorless crystals, mp 244-245 C.

Reference： [1]Patent: US4444774,1984,A

47
[ 4923-01-7 ]
[ 582-73-0 ]
[ 90815-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	In acetic acid	11 2-Methyl-7-(3-pyridinyl)-5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin EXAMPLE 11 2-Methyl-7-(3-pyridinyl)-5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin A reaction mixture of 0.986 g of 3-amino-5-methyl-1,2,4-triazole and 2.178 g of 4,4,4-trifluoro-1-(3-pyridyl)-1,3-butanedione in 25 ml of glacial acetic acid was refluxed for 4 hours. The mixture was then evaporated to dryness in vacuo and gave a crystalline residue. This residue was partitioned between a saturated aqueous sodium bicarbonate solution and dichloromethane and the procedure of Example 1 was continued to give 1.33 g of the desired product as colorless crystals, mp 195°-197° C.

Reference： [1]Current Patent Assignee: PFIZER INC - US4444774, 1984, A

48
[ 4923-01-7 ]
[ 33884-41-2 ]
[ 727997-38-8 ]

Yield	Reaction Conditions	Operation in experiment
67%	With acetic acid Reflux; regioselective reaction;

Reference： [1]Location in patent: experimental part Shikhaliev; Krylski; Potapov; Nefedov; Sidorenko [Russian Chemical Bulletin, 2008, vol. 57, # 6, p. 1268 - 1272]

49
[ 141-97-9 ]
[ 4923-01-7 ]
[ 51596-06-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With acetic acid; for 6h;Reflux;	[0163] Synthesis of 2,5-Dimethyl-[l,2,4]triazolo[l,5-alpha]pyrimidin-7-yI)-naphthalen-2- yl-amine.; [0164] This compound is synthesized according the scheme above and is characterized as follows: melting point: 84C. 1H NMR (300 MHz, DMSO-d6): delta 10.32 (brs, NH, exchangeable), 8.05-7.90 (m, 4H), 7.52-7.60 (m, 3H), 6.48 (s, IH), 2.50 (s, 3H), 2.36 (s, 3H). MS m/z 290.1 (M + H+).

Reference： [1]Patent: WO2009/82691,2009,A1 .Location in patent: Page/Page column 33

50
[ 24945-13-9 ]
[ 4923-01-7 ]
[ 1239270-28-0 ]

Yield	Reaction Conditions	Operation in experiment
49%	Stage #1: 2,2-dimethyltetrahydropyran-4-ol With dipyridinium dichromate In tetrahydrofuran at 20℃; for 3h; Molecular sieve; Stage #2: 5-methyl-4H-1,2,4-triazol-3-amine With sodium cyanoborohydride; acetic acid at 20℃; for 16h;	119 Reference Example 119N-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-5-methyl-4H-1,2,4-triazol-3-amineA mixture of 2,2-dimethyltetrahydro-2H-pyran-4-ol (5 g), pyridinium dichromate (22 g), molecular sieves 4 A (22 g) and tetrahydrofuran (200 mL) was stirred at room temperature for 3 hr. The reaction solution was diluted with diethyl ether (200 mL), the insoluble material was filtered off through silica gel, and the filtrate was concentrated. The obtained residue was dissolved in acetic acid (30 mL), 5-methyl-4H-1,2,4-triazol-3-amine (2.5 g) and sodium cyanoborohydride (11 g) were added, and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.6 g, 49%).1H NMR (300 MHz, DMSO-d6) δ 1.03-1.30 (m, 8H), 1.70-1.85 (m, 2H), 2.07 (br.s., 3H), 3.48-3.66 (m, 3H), 5.17-6.39 (m, 1H), 11.47-12.45 (m, 1H)

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2010/197683, 2010, A1 Location in patent: Page/Page column 66

51
[ 874-42-0 ]
[ 105-45-3 ]
[ 4923-01-7 ]
C₁₅H₁₄Cl₂N₄O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4395 - 4398

52
[ 4923-01-7 ]
[ 17838-69-6 ]
[ 1225549-79-0 ]

Reference： [1]Heterocycles,2010,vol. 80,p. 1149 - 1163
[2]Bioorganic Chemistry,2010,vol. 38,p. 265 - 270

53
[ 4923-01-7 ]
[ 89809-67-6 ]
[ 1234620-75-7 ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 65℃; for 12h;Inert atmosphere;	Example 20A (rac)-Ethyl 7-(4-cyanophenyl)-2,5-dimethyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate Under an atmosphere of argon, ethyl 2-(4-cyanobenzylidene)-3-oxobutanoate (381 mg, 1.6 mmol) and 5-methyl-4H-1,2,4-triazole-3-amine (200 mg, 2.0 mmol, 1.3 eq.) were dissolved in DMF (4 ml), and solid sodium bicarbonate (659 mg, 7.8 mmol, 5 eq.) was added. The mixture was stirred at 65 C. for 12 h. The mixture was then filtered, and the DMF from the filtrate was distilled off under reduced pressure. The residue was purified by preparative HPLC (Gromsil C18 column, 30*250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (300 mg, 46% of theory). LC-MS (Method 2): Rt=1.92 min; MS (ESIpos): m/z (%)=324.1 (100) [M+H]+; MS (ESIneg): m/z (%)=322.1 (100) [M-H]-. 1H-NMR (400 MHz, DMSO-d6): delta=1.0 (t, 3H), 2.1 (t, 3H), 2.4 (s, 3H), 3.4 (m, 2H), 6.25 (s, 1H), 7.4 (m, 2H), 7.8 (m, 2H), 10.75 (s, 1H).

Reference： [1]Patent: US2012/4203,2012,A1 .Location in patent: Page/Page column 32

54
[ 4923-01-7 ]
[ 83-13-6 ]
[ 1116117-17-9 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 25. Og 3-amino-5-methyltriazole and 66.0ml_ diethyl phenylmalonate in 100ml_ N,N-dibutylbutan-1 -amine was stirred at 185C for 20h. The reaction mixture consisted of two layers after cooling to room temperature. The top layer was removed and the lower layer was diluted with 10% w/w sodium hydroxide solution and water. The aqueous layer was extracted with diethyl ether and acidified with concentrated hydrochloric acid until precipition of the product was complete. The precipitate was collected by filtration to yield the product, which was used without further purification.MS (M+1 ): 243Characteristic 1 H NMR (200MHz, d6-DMSO) signals: 7.4 (m, 2H); 7.3 (m, 2H); 7.2 (m, 1 H); 2.4 (s, 3H) ppm.

Reference： [1]Patent: WO2012/7416,2012,A1 .Location in patent: Page/Page column 79; 80

55
[ 1522-41-4 ]
[ 4923-01-7 ]
[ 1353761-12-2 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2011,vol. 47,p. 1164 - 1169

56
[ 1522-41-4 ]
[ 4923-01-7 ]
[ 1353761-09-7 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2011,vol. 47,p. 1164 - 1169

57
[ 4923-01-7 ]
[ 105-53-3 ]
C₆H₈N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium ethanolate; In ethanol; at 75℃; for 18h;	General procedure: A solution of 21% (w/v) sodium ethoxide (9.13 mL, 24.46 mmol) in ethanol was added to a solution of <strong>[4923-01-7]3-methyl-1H-1,2,4-triazol-5-amine</strong> (2 g, 20.39 mmol) and diethylmalonate (3.42 mL, 22.42 mmol) in Ethanol (10 mL) in a 100 mL round bottomed flask. The resulting mixture was stirred at 75 C overnight. The reaction mixture was cooled and the resulting precipitate was filtered and rinsed with EtOH. The solid was air dried to yield an off white solid (2.84g, 84%). 1H NMR (400 MHz, DEUTERIUM OXIDE) ppm 2.21 (s, 3 H) 4.87 (s, 1 H); LC/MS: MS(ES+) m/e 167 (MH+).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3198 - 3202

58
[ 65157-84-8 ]
[ 4923-01-7 ]
[ 1435464-72-4 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2013,vol. 68,p. 175 - 181

59
[ 1028843-08-4 ]
[ 4923-01-7 ]
[ 1029520-84-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 72 - 76

60
[ 2582-30-1 ]
[ 64-19-7 ]
[ 4923-01-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	With nitric acid; In water; for 45h;pH 4;Reflux;	To a solution of (diaminomethyl)hydrazine carbonic acid salt (11 g, 80.3 mmol) in water (30 ml) was added dropwise AcOH (9.6 g, 160 mmol) at room temperature. The pH was adjusted 4 with HNO3 (0.1 ml, cone), and the reation mixture was stirred for 45 h at reflux. The resulting mixture was concentrated under vacuum to give a residue, which was purified by a silica gel column (2% ~ 20% methanol in dichloromethane) to afford 3 -methyl- lH-l ,2,4-triazol-5 -amine as a white solid (4 g, 50 %). LC/MS (ES, m/z): [M+H]+ 99.0 *H NMR (300 MHz, DMSO) delta 1.84 (s, 3H)

Reference： [1]Patent: WO2014/66743,2014,A1 .Location in patent: Paragraph 0146

61
[ 1607025-37-5 ]
[ 4923-01-7 ]
[ 1607425-95-5 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In diphenylether; at 170℃; for 1h;	To a solution of 3-methyl- lH-l ,2,4-triazol-5-amine (150 mg, 1.52 mmol) in diphenyl ether (2 ml) was added ethyl 3-(l -acetyl- lH-indazol-5-yl)-3- oxopropanoate (710 mg, 2.59 mmol), TsOH (1 1 mg, 0.06 mmol), and the mixture was stirred for 1 h at 170C. The resulting solution was diluted with petroleum ether (8 ml), and solids were collected by filtration and washed with ethyl ether (3 ml) to afford 5-(l -acetyl- lH-indazol-5-yl)-2-methyl-[l ,2,4]triazolo[l ,5-fl]pyrimidin- 7(4H)-one as a crude brown solid(100 mg, crude). LC/MS (ES, m/z): [M+H]+ 309.0

Reference： [1]Patent: WO2014/66743,2014,A1 .Location in patent: Paragraph 0146

62
[ 74053-94-4 ]
[ 4923-01-7 ]
[ 1607425-75-1 ]

Yield	Reaction Conditions	Operation in experiment
12%	With acetic acid; at 120℃; for 16h;	A mixture of 5-methyl-2H-l ,2,4-triazol-3-amine (147 mg, 1.50 mmol, 1.00 equiv), acetic acid (3 mL), and ethyl 3-(2,3-dihydrobenzo[^][l,4]dioxin-6-yl)-3- oxopropanoate (375 mg, 1.50 mmol, 1.00 equiv) was stirred for 16 hr at 120C, then concentrated to dryness. The resulting solid was washed by 5 mL MeOH and collected by filtration. The solid was dissolved in 10 mL of NH4OH (aq.) and filtered. The filtrate was adjusted to pHLC-MS: (ES, m/z): 285 [M+H]+ *H NMR (300MHz, DMSO, ppm): 13.40 (s, 1H), 7.48-7.42 (m, 2H), 7.00 (s, 1H), 6.31 (s, 1H), 4.31 (t, /=4.8Hz, 4H), 2.41 (s, 3H)

Reference： [1]Patent: WO2014/66743,2014,A1 .Location in patent: Paragraph 0146

63
[ 21577-50-4 ]
[ 4923-01-7 ]
[ 1250444-41-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium acetate In ethanol; water at 95℃; for 12h;

Reference： [1]Krishnaraj, Thulasiraman; Muthusubramanian, Shanmugam [Journal of Heterocyclic Chemistry, 2014, vol. 51, # SUPPL. 1, p. E68-E70]

64
[ 368869-97-0 ]
[ 4923-01-7 ]
2-(2,3-dihydrobenzofuran-5-yl)-N-(3-methyl-1H-1,2,4-triazol-5-yl)thiazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With pyridine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; at 110℃; for 5h;	2-(2,3-Dihydrobenzofuran-5-yl)-N-(3-methyl-1H-1,2,4-triazol-5-yl)thiazole-4- To a mixture of 2-(2,3-dihydro-l-benzoruran-5~yl)-l,3-thiazole-4-carboxylic acid (126 mg, 0.51 mmol), lH-l ,2,4-triazol-5-amine (50 mg, 0.51 mmol) and 2-(lH-benzotriazole-l-yl)- 1 ,1 ,3,3-tetramethyluroniurn hexafluorophosphate (HBTU) (120 mg, 0.32 mmol) under stirring and heating at 1 10 C 2 ml of dry pyridine were added. The mixture was heated at 110 C for 5 h, pyridine was evaporated, and the residue was diluted with an aqueous Na2C03 solution. The resulting precipitate was filtered off, dissolved in hot NN-dimethylformamide, settled by addition of EtOAc and hexane, filtered off and dried. The product was obtained as a light yellow solid (82 mg, 0.25 mmol, 49 % yield). NMR (400 MHz, OMSO-d6, CC14) delta ppm 2.29 (3 H, bs, CH3), 3.30 (2 H, t, CH2CH20), 4.64 (2 H, t, OCH2), 6.80 (1 H, d, CH-arom.), 7.82 (1 H, d, CH-arom.), 8.00 (1 H, s, CH-arom.), 8.31 (1 H, bs, CH-thiazol), 1 1.20 (1 H, bs, NH), 12.95 (1 H, bs, NH). LC/MS [M+H]+: 328.0

Reference： [1]Patent: WO2014/202638,2014,A1 .Location in patent: Page/Page column 96

65
[ 4923-01-7 ]
[ 87-13-8 ]
[ 99179-11-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With acetic acid; at 120℃; for 3h;	General procedure: A solution of aminotriazole 11a-m (3.1mmol), glacial acetic acid (5mL), and diethyl ethoxymethylenemalonate (4.6mmol) was refluxed for 3h. After cooling to room temperature, the resulting precipitate was collected by filtration, washed with cold water and dried. The residue was stirred with cold ethyl ether (20mL) and filtered to afford the desired product. Following general procedure C, compound 12b was isolated as a pale yellow solid 70%, mp=237C dec. 1H NMR (200MHz, DMSO-d6) delta: 12.9 (br s, 1H); 8.58 (s, 1H); 4.28-4.17 (q, J=7.4Hz, 2H); 2.38 (s, 3H); 1.31-1.27 (t, J=7Hz, 3H)

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 113,p. 11 - 27
[2]Archiv der Pharmazie,2019,vol. 352
[3]Bioorganic Chemistry,2020,vol. 94

66
[ 4923-01-7 ]
ethyl nitrocyanoacetate potassium salt [ No CAS ]
C₅H₄N₇O₂^(1-)*K⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Solution A. A solution of KOH (0.56 g, 0.01 mol) and potassium salt of ethyl nitrocyanoacetate (1.96 g, 0.01 mol) in2 (8 ml) was stirred at room temperature for 3 h, then kept overnight. 4 M aqueous KOAc (8 ml, 0.03 mol) was added to the resulting solution, and the mixture cooled to 5. A mixture of 3-aminoazole 1a-i (0.010 mol), EtOH (10 ml),H2O (10 ml), and concentrated HCl (2.5 ml, 0.030 mol)was treated with a solution of NaNO2 (0.759 g, 0.011 mol)in H2O (3 ml) at -5 . The reaction mixture was kept at this temperature for 10 min, then added to the solution A. The mixture was kept at room temperature for 1 h; the formed precipitate was filtered, stirred with 40% aqueous H2SO4 (10 ml) (AcOH (10 ml) was used for compound 4e), filtered, and dried. The obtained hydrazone 3a-i was heated under reflux in DMF for 3 h. The solvent was evaporated, the residue triturated in water, filtered, and dried.

Reference： [1]Chemistry of Heterocyclic Compounds,2015,vol. 51,p. 1057 - 1060
Khim. Geterotsikl. Soedin.,2015,vol. 51,p. 1057 - 1060,4

67
[ 2065-75-0 ]
[ 4923-01-7 ]
6-bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With acetic acid; at 60℃; for 18h;Inert atmosphere;	<strong>[4923-01-7]3-methyl-1H-1,2,4-triazol-5-amine</strong> (4.7747 g, 48.7 mmol, 1 eq.) and 2- bromomalonaldehyde (8.08 g, 53.5 mmol, 1.1 eq.) were dissolved in AcOH (50 ml) and heated15 at 60 C for 18 hours under inert conditions. The reaction mixture was concentrated under vacuo, then the crude material was redissolved in EtOAc and filtered. The filtrate was combined with NaHCO3, and the aqueous layer was extracted with EtOAc (x3). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude material was absorbed onto silica and purified by column chromatography (Si02, 100% DCM, then 98:2 DCM:MeOH)20 to give 6-bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine (2.22g, 21%, mlz: 215.1 [M+H]+) as an off-white solid.

Reference： [1]Patent: WO2016/184832,2016,A1 .Location in patent: Page/Page column 37

68
[ 4923-01-7 ]
[ 105-53-3 ]
sodium salt of 7-methyl-4-oxo-1,4-dihydro-1,2,4-triazolo[5,1-c][1,2,4]triazin-3-carboxylic acid ethyl ester dihydrate [ No CAS ]

Reference： [1]Archiv der Pharmazie,2017,vol. 350

69
[ 26510-52-1 ]
[ 4923-01-7 ]
2-methyl-5-(pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With acetic acid; at 115℃; for 12h;Inert atmosphere;	(a) Ethyl 3-oxo-3-(pyridin-2-yl)propanoate (400mg, 2.07mmol) was taken in AcOH (10mL) in a 50mL round bottom flask under N2. To it was added 5-methyl-4H-1,2,4-triazol-3-amine (334mg, 2.49mmol). The reaction mixture was heated at 115C for 12h. The reaction mixture was then evaporated to dryness using toluene as an azeotropic solvent and triturated with diethyl ether. This was finally dried under high vaccum which affored 66a as a brown solid (350mg, 75%). This was then used in the next step without any further purification. LCMS(ESI) m/z 226.03 [M-H+]; 56% (purity).

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 3922 - 3946

70
potassium salt of nitroacetaldehyde [ No CAS ]
[ 4923-01-7 ]
[ 107753-07-1 ]

Reference： [1]Mendeleev Communications,2017,vol. 27,p. 285 - 286

71
[ 90-02-8 ]
[ 4923-01-7 ]
[ 67-64-1 ]
2,5-dimethyl-11,12-dihydro-5,11-methano[1,2,4]triazolo[1,5-c][1,3,5]benzoxadiazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With hydrogenchloride; In 1,4-dioxane; ethanol; at 150℃; for 0.5h;Microwave irradiation; Sealed tube;	General procedure: 3-Amino-1,2,4-triazole 8a-f (1.0 mmol), o-hydroxybenzaldehyde9a-e (1.0 mmol), acetone (10) (0.22 ml,3.0 mmol), and abs. EtOH (2 ml) were mixed in amicrowave process vial, and then 4 N solution of HCl indioxane (0.07 ml, 0.3 mmol) was added. The mixture wasirradiated at 150C for 30 min. The reaction mixture wascooled by an air flow and stirred for 24 h at roomtemperature for complete precipitation of the product. Theprecipitate was filtered off, washed with EtOH (1 ml) andEt2O (3×1 ml), and dried. Compounds 1a-w were obtainedin a form of white solids.2,5-Dimethyl-11,12-dihydro-5,11-methano[1,2,4]triazolo[1,5-c][1,3,5]benzoxadiazocine (11a). Yield 48%,mp 310-311C. IR spectrum, nu, cm-1: 757, 1091, 1138,1325, 1485, 1548, 1625, 2885, 2922, 3070, 3421. 1H NMRspectrum, delta, ppm: 7.76 (1H, s, NH); 7.33-7.26 (1H, m,H Ar); 7.20-7.12 (1H, m, H Ar); 6.98-6.90 (1H, m, H Ar);6.82-6.76 (1H, m, H Ar); 4.52 (1H, s, 11-CH); 2.30 (2H, s,13-CH2); 2.02 (3H, s, 2-CH3); 1.91 (3H, s, 5-CH3).13C NMR spectrum, delta, ppm: 157.3 (C); 153.9 (C); 151.0(C); 130.0 (CH); 129.4 (CH); 124.4 (C); 121.2 (CH); 116.7(CH); 82.3 (C); 44.3 (CH); 32.3 (CH2); 24.0 (CH3); 14.2(CH3). Mass spectrum, m/z: 242 [M]+. Found, %: C 64.34;H 5.54; N 23.29. C13H14N4O. Calculated, %: C 64.45;H 5.82; N 23.12.