ChemicalBook CAS DataBase List 5-METHYL-[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE

5-METHYL-[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE synthesis

7synthesis methods

Product Name:5-METHYL-[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE
CAS Number:15562-30-8
Molecular formula:C6H6N4
Molecular Weight:134.14

5436-21-5 Synthesis

5436-21-5
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61-82-5 Synthesis

61-82-5
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5-METHYL-[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE

15562-30-8
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Yield:15562-30-8 47%

Reaction Conditions:

with methanol;sodium methylate at 20; for 24 h;Temperature;

Steps:

1.4.1. 5-Methyl[1,2,4]triazolo[1,5-a]pyrimidine (3a).

Method A. Acetoacetaldehyde dimethylacetal solution (2.64 g, 20 mmol) in MeOH (1.4 mL) was added dropwise to the mixture of 3-amino-1,2,4-triazole (1.68 g, 20 mmol) and MeONa solution (0.71 mol/L, 14 mL) under stirring. The resulting mixture was stirred for 24 h at room temperature, then was filtered and was diluted with MeOH (2 mL) to give pure compound 3a (1.26 g, 47 %). Method B. A solution of 3-amino-1,2,4-triazole (1.68 g, 20 mmol) and acetoacetaldehyde dimethylacetal (2.64 g, 20 mmol) in DMF (1 mL)was refluxed for 1 h. The resulting mixture was allowed to stand for 24 h in cold, filtered and was diluted with MeOH (2 mL) to give pure compound 3a (1.10 g, 41 %). White solid; mp 167-170 °C. ν_max(KBr) 1537,1617, 1629, 1843, 2930, 3014, 3076, 3120 cm^-1; δ_H(200 MHz, DMSO-d₆) 9.22 (1H, d, J = 7.0, C(7)H), 8.55 (1H, s, C(2)H), 7.23 (1H, d, J = 7.0, C(6)H), 2.60 (3H, s,CH₃); δ_C(125 MHz, DMSO-d₆) 165.70, 155.63, 154.46, 136.32, 111.65, 24.71; m/z (EI, 70 eV): 134 (M⁺, 34), 84 (100),49 (84). Anal. Calcd. for C₆H₆N₄ (134.14): C, 53.72; H, 4.51; N, 41.77 %. Found: C, 53.87; H, 4.53; N, 41.59 %.

References:

Kolosov, Maksim A.;Shvets, Elena H.;Manuenkov, Dmitriy A.;Vlasenko, Sergey A.;Omelchenko, Irina V.;Shishkina, Svetlana V.;Orlov, Valeriy D. [Tetrahedron Letters,2017,vol. 58,# 12,p. 1207 - 1210] Location in patent:supporting information