Silver mediated preparation method and application of 4-substituted-2-amino-5-fluoropyrimidine compound
A compound, fluoropyrimidine technology, applied in the field of preparation of 4-substituted-2-amino-5-fluoropyrimidine compounds, achieving the effects of mild conditions, wide application range of substrates, and short reaction time
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Embodiment 1～22
[0026] Described embodiment 1~22 reaction formula is as follows:
[0027]
[0028] Taking 4-phenyl-2-aminopyrimidine substrate as an example, screen the appropriate fluorine source, silver salt, temperature, and solvent. Wherein Fsource refers to the fluorine source, Ag salt refers to the silver salt, Solvent refers to the reaction solvent, and T refers to the reaction temperature.
[0029] The concrete preparation method of described embodiment 1~22 is as follows:
[0030] Add 4-phenyl-2-aminopyrimidine, fluorine source, silver salt, and reaction solvent into the reaction tube, control the reaction temperature, cool to room temperature after 2 hours of reaction, add 1.0 equivalent of trifluorotoluene as internal standard, and pass NMR Fluorine spectrum to check the yield.
[0031] Described embodiment 1~22 are shown in the following table:
[0032]
[0033] Wherein, NFSI is N-fluorobisbenzenesulfonamide;
[0034] Selectfluor belongs to the product name and is a fluo...
Embodiment 23～39
[0037] The aminopyrimidine substrate was expanded under the preferred conditions of Example 8 to carry out the operations of Examples 23-39.
[0038] Described embodiment 23~39 reaction formulas are as follows:
[0039]
[0040] Wherein R can be aryl, styryl or anilino.
[0041] The concrete preparation method of described embodiment 23~39 is as follows:
[0042] Weigh 0.1 mmol of 4-substituted-2-aminopyrimidine substrate, 0.12 mmol of Selectfluor and 0.2 mmol of silver carbonate respectively, add to the reaction tube in one pot, add 2 ml of analytically pure acetonitrile into the reaction tube, The reaction tube was closed and placed in an oil bath at 70°C for about 2 hours. After the reaction, cooled to room temperature, acetonitrile was distilled off under reduced pressure, and the residue was separated by silica gel thin layer chromatography (petroleum ether / ethyl acetate=5 / 1, v / v) to obtain the target product 4-substituted-2-amino- 5-fluoropyrimidines.
Embodiment 23
[0044] Example 23: The target product is 4-phenyl-2-amino-5-fluoropyrimidine
[0045]
[0046] White solid, yield: 61%, melting point: 165.4–166.9°C.
[0047] 1H NMR (400MHz, CDCl 3 ):δ8.23(d,J HF =3.4Hz,1H),8.07–7.98(m,2H),7.52–7.46(m,3H),5.08(s,2H). 13 C NMR (101MHz, CDCl 3 ):δ159.64(d,J CF =3.1Hz), 152.61(d,J CF =9.6Hz), 150.72(d,J CF =251.8Hz), 147.02(d, J CF =26.2Hz), 133.49(d, J CF =5.2Hz), 130.77, 128.93(d, J CF =6.2Hz), 128.61. 19 F NMR (376MHz, CDCl 3 ):δ-152.49(s,1F).IR(KBr):ν max (cm -1 )=3323,3175,1652,1558,1473,1355,1274,1200.HRMS(ESI-TOF)m / zcalcd.for C 11 h 9 FN 3 + [M+H] + :190.0775; found: 190.0743.
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