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ChemicalBook CAS DataBase List 5,7-dichloro-3-isopropylpyrazolo[1,5-a]pyrimidine

5,7-dichloro-3-isopropylpyrazolo[1,5-a]pyrimidine synthesis

6synthesis methods
771510-25-9 Synthesis
3-isopropylpyrazolo[1,5-a]pyrimidine-5,7-diol

771510-25-9
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5,7-dichloro-3-isopropylpyrazolo[1,5-a]pyrimidine

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Yield: 81%

Reaction Conditions:

with trichlorophosphate for 16 h;Heating / reflux;

Steps:

22.1
5,7-Dichloro-3-isopropylpyrazolo[l,5-«]pyrimidine (ICEC0005); [00222] To a suspension of 3-Isopropyl-5,7-dihydroxypyrazolo[l,5-a]pyrimidine(ICEC0004) (3.95 g, 20.4 mmol) in POCl3 (38.2 mL, 410 mmol) was added N,N- dimethylaniline (1.73 mL, 13.6 mmol) and the mixture was heated under reflux for 16 h. During this time the pyrimidine went into solution. The POCl3 was distilled off and the concentrate poured onto ice (~ 50 g). The product was extracted with extracted with CH2Cl2 (3 x 50 mL) and the combined organic fractions were washed with brine and dried over Na2SO4. After concentration the crude product was purified by column chromatography on silica (ethyl acetate:hexanes = 1 :20) to yield the title compound ICEC0005 as a yellow solid (3.81 g, 81%).[00223] M.p. 43-44°C (ethyl acetate). 1H NMR (CDCl3, 300 MHz) δ 8.10 (s, IH), 6.93(s, IH), 3.31 (hep, J = 6.8 Hz, IH), 1.37 (d, J = 6.8 Hz, 6H). 13C NMR (CDCl3, 75 MHz) δ 147.3, 144.6, 143.9, 139.4, 119.4, 107.9, 23.6, 23.2. IR (neat) vmax = 2963, 1641, 1496, 1098, 618. MS m/z (CI) 230 (M+H). HRMS (CI) CaIc: 230.0252; Found: 230.0248 Microanalysis CaIc: C 46.98, H 3.94, N 18.26; Found: C 47.02, H 3.87, N 18.28.

References:

EMORY UNIVERSITY;IMPERIAL COLLEGE OF SCIENCE AND TECHNOLOGY;JOGALEKAR, Ashutosh, S. WO2008/151304, 2008, A1 Location in patent:Page/Page column 113-115

771510-25-9 Synthesis
3-isopropylpyrazolo[1,5-a]pyrimidine-5,7-diol

771510-25-9
18 suppliers
inquiry

5,7-dichloro-3-isopropylpyrazolo[1,5-a]pyrimidine

771510-32-8
77 suppliers
inquiry