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[ CAS No. 2503-56-2 ]

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Chemical Structure| 2503-56-2
Chemical Structure| 2503-56-2
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CAS No. :2503-56-2 MDL No. :MFCD00005555
Formula : C6H6N4O Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :150.14 g/mol Pubchem ID :75629
Synonyms :

Safety of [ 2503-56-2 ]

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 [ 2503-56-2 ]

  • Upstream synthesis route of [ 2503-56-2 ]
  • Downstream synthetic route of [ 2503-56-2 ]

[ 2503-56-2 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 2503-56-2 ]
  • [ 24415-66-5 ]
YieldReaction ConditionsOperation in experiment
65% With triethylamine; trichlorophosphate In 1,4-dioxane at 105℃; for 3 h; A solution of 3 (1.60 g; 10.66 mmol) in dioxane (10 mL) was added POCl3 (2.5 mL; 26.65 mmol) and Et3N (2.97 mL; 21.32 mmol). The solution was heated at 105 °C for 3h. The reaction was followed by TLC. After completion, the reaction was allowed to cool to room temperature and NaHCO3 solution was added dropwise until to pH=8. Then DCM was added and the phases were separated. The aqueous layer was extracted with DCM. The organic phase was dried (MgSO4) and filtered. The solvent was evaporated under reduced pressure giving oil which was purified by column chromatography. Using a solvent gradient from neat petroleum ether to 50percent AcOEt/petroleum ether, compound 4 was obtained as a yellow solid (1.16 g, 65percent).
65% for 0.5 h; Heating / reflux To 0.976 g (6.50 mmol) 5- Methyl-[l,2,4]triazolo[l,5-α]-pyrimidin-7-ol, in a round bottom flask, was added 1.82 mL (19.50 mmol) of phosphorus oxychloride, and the mixture was heated under reflux for 30 minutes, during which time the solid dissolved and hydrogen chloride evolved. The excess phosphorus oxychloride was removed by distillation at reduced pressure on a steam-bath, and the residue triturated with ice water. The product was extracted from the aqueous mixture with methylene <n="26"/>chloride. The resulting solution was evaporated and purified by column chromatography to give the product with 65percent (0.710 g) yield.
55% at 110℃; for 1.5 h; The proper 5- Methyl-[1,2,4] triazolo [1,5-a] Pyrimidin-7-ol (10 mmol) was added to 2.75 ml (30 mmol) of phosphorous oxychloride and heated under reflux for 90 min in a round bottom flask. Excess phosphorous oxychloride was removed by distillation at reduced pressure on a steam bath, and the residue was triturated with ice water. The product was extracted from the aqueous mixture with CH2Cl2, evaporated, and purified by column chromatography using 60percent EtOAc/hexane. Yield of the product is 55percent. 4.1.4.1. 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine (8). White-yellow solid (Rf = 0.6 in pure ethyl acetate); m.p. 150 °C.; 1H NMR (300 MHz, CDCl3): δ 8.50 (s, 1H, Triazolopyrimidine-Hb), 7.15 (s, 1H, Triazolopyrimidine-Ha), 2.75 (s, 3H, Triazolopyrimidine-CH3)LCMS: (ESI, m/z): [M+H]+ calcd for C5H6ClN4 169.1; found: 169.1.
55% at 110℃; for 1.5 h; The formed 5-Methyl-[1,2,4] triazolo [1,5-a]Pyrimidin-7-ol (1.0 equiv) was added to 2.75 mL (3.0 equiv) of phosphorous oxychloride and heated under reflux for 90 min in a round bottom flask. Excess phosphorous oxychloride was removed under reduced pressure on a rotatory evaporator, and the residue was triturated with ice water. The product was extracted from the aqueous mixture with CH2Cl2, organic layer was dried over sodium sulphate, evaporated at reduced pressure, and purified by column chromatography using 60percent EtOAc/hexane. 4.2.2.1. 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine (7). White-yellow solid; Yield: 55percent; mp: 150 °C; ESI-MS: m/z 169.1[M+H]+; 1H NMR (300 MHz, CDCl3): δ 8.50 (s, 1H, Triazolopyrimidine-Hb), 7.15 (s, 1H, Triazolopyrimidine-Ha), 2.75 (s, 3H, Triazolopyrimidine-CH3).
40%
Stage #1: for 1.5 h; Reflux
Stage #2: Cooling
b. A solution of 5-methyl-[l,2,4]triazolo[l,5-a]pyrimidin-7-ol (54) (2 g, 13.32 mmol) in phosphorous oxy chloride (8.23 g, 53.64 mmol) was heated at reflux for 1.5 h. The reaction mixture was cooled to room temperature and concentrated in vacuum to dryness. The residue obtained was quenched by adding ice water and extracted with ethyl acetate (2 x 100 mL). The organic layers were combined washed with water (2 x 50 mL), brine (50 mL), dried and concentrated in vacuum. The residue obtained was purified by flash column chromatography [silica gel 12 g, eluting with ethyl acetate and methanol (9:1) in hexanes 0 to 50percent] to afford 7-chloro-5-methyl- [l,2,4]triazolo[l,5-a]pyrimidine (55) (900 mg, 40.0percent) as light yellow solid. 1HNMR (300 MHz, DMSO) δ 8.76 - 8.61 (m, IH), 7.64 (d, J= 14.6, IH), 2.63 (s, 3H); MS (ES4), 169.2 (M+l), 191.1 (M+Na); Analysis: Calcd for C6H5ClN4: C, 42.74; H, 2.98; N, 33.23; Found: C, 42.83; H, 2.91; N, 33.25.

Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 11, p. 1050 - 1054
[2] Patent: WO2007/149211, 2007, A1, . Location in patent: Page/Page column 23-24
[3] Monatshefte fuer Chemie, 1987, vol. 118, p. 601 - 606
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 7, p. 1864 - 1872
[5] European Journal of Medicinal Chemistry, 2016, vol. 119, p. 260 - 277
[6] European Journal of Medicinal Chemistry, 2017, vol. 136, p. 36 - 51
[7] Patent: WO2010/14930, 2010, A2, . Location in patent: Page/Page column 52
[8] Journal of Medicinal Chemistry, 2008, vol. 51, # 12, p. 3649 - 3653
[9] Journal of Medicinal Chemistry, 2011, vol. 54, # 11, p. 3935 - 3949
[10] Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 4, p. 317 - 320
[11] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 15, p. 3922 - 3946
[12] Patent: WO2009/82691, 2009, A1, . Location in patent: Page/Page column 36-37
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