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Y. Ren et al. / Bioorg. Med. Chem. 19 (2011) 7501–7506
4.5.1.3. 2-Methyl-5-((4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl)
methyl)pyrimidin-4-amine (3c). White solid; yield 90%; mp
132–133 °C. 1H NMR (600 MHz, CDCl3) d (ppm): 2.50 (s, 3H,
CH3), 5.18 (s, 2H, OCH2), 5.35 (s, 2H, CH2), 5.59 (s, 2H, NH2),
6.95–6.99 (m, 3H, Ar-H), 7.27–7.30 (t, 2H, J = 7.8 Hz, Ar-H), 7.62
(s, 1H, triazole CH), 8.19 (s, 1H, pyrimidine CH). ESI-MS m/z: 297
(M+1)+. Anal. calcd for C15H16N6O: C, 60.80; H, 5.44; N, 28.36.
Found: C, 60.62; H, 5.35; N, 28.60.
Leader in Wuhan Municipality (No. 201150530150), the self-deter-
mined research funds of CCNU from the colleges’ basic research
and operation of MOE (Nos. CCNU09A01010, CCNU10C01002,
and CCNU10A02006), and the research was also supported in part
by the PCSIRT (No. IRT0953).
References and notes
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4.5.1.4. Ethyl 4-((1-((4-amino-2-methylpyrimidin-5-yl)methyl)-
1H-1,2,3-triazol-4-yl)methoxy)benzoate (3d). White solid; yield
94%; mp 190–192 °C. 1H NMR (400 MHz, DMSO-d6) d (ppm):1.28-
1.31 (t, 3H, J = 10.2 Hz, 10.8 Hz, CH3), 2.30 (s, 3H, CH3), 4.24–4.29
(q, 2H, J = 10.8 Hz, CH2), 5.22 (s, 2H, OCH2), 5.45 (s, 2H, CH2), 6.93
(s, 2H, NH2), 7.12-7.14 (d, 2H, J = 12.6 Hz, Ar-H), 7.89–7.91 (d, 2H,
J = 12.6 Hz, Ar-H), 8.01 (s, 1H, triazole-CH), 8.24 (s, 1H, pyrimidine
CH). ESI-MS m/z: 369 (M+1)+. Anal. calcd for C18H20N6O3: C, 58.69;
H, 5.47; N, 22.81. Found: C, 58.88; H, 5.59; N, 22.62.
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The stirred reaction mixture of 3d (0.37 g, 1 mmol) and LiOH
monohydrate (126 mg, 3 mmol) dissolved in THF/MeOH/H2O
(2:1:1, 12 mL) was stirred at room temperature until the reaction
was complete based on TLC monitoring. Then the solvent was re-
moved under reduced pressure. The residue was dissolved in water
and quench the mixture with dilute HCl solution to pH = 3. The
precipitate was collected by filtration, washed with little THF and
dried in the atmospheric pressure.
4.5.2.1. 4-((1-((4-Amino-2-methylpyrimidin-5-yl)methyl)-1H-
1,2,3-triazol-4-yl)methoxy)benzoic acid (3e). White solid; yield
76%; mp >260 °C. 1H NMR (400 MHz, DMSO-d6) d (ppm): 2.34 (s,
3H, CH3), 5.22 (s, 2H, OCH2), 5.47 (s, 2H, CH2), 7.11–7.13 (d, 2H,
J = 13.2 Hz, Ar-H), 7.20 (s, 2H, NH2), 7.88–7.90 (d, 2H, J = 12.6 Hz,
Ar-H), 8.06 (s, 1H, triazole-CH), 8.26 (s, 1H, pyrimidine CH). ESI-
MS m/z: 341 (M+1)+. Anal. calcd for C16H16N6O3: C, 56.47; H,
4.74; N, 24.69. Found: C, 56.35; H, 4.74; N, 24.45.
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This work was supported by the National Basic Research Pro-
gram of China (973 Program, No. 2010CB126100), the Natural Sci-
ence Foundation of China (Nos. 20873049, 20872044, 21072073,
21172089, 20372023 and 21172090), Natural Science Foundation
of Hubei Province (No. 2010CDB01202), the Program for Academic