A practical strategy for the synthesis of 2-dialkylamino-4-arylamino-6-aminopyrimidines

Tetrahedron Letters

Volumn 50, Issue 43, 2009, Pages 5888-5893

  Li, Chaomin ^a   Rosenau, Andrew ^a  

^a Merck Research Laboratories Boston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 AMINOPYRIMIDINE; BUSPIRONE; DOXAZOSIN; IMATINIB; PYRIMIDINE DERIVATIVE; ROSUVASTATIN; TRIMETHOPRIM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 69749108869     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.154     Document Type: Article

References (20)

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15. Montebugnoli D., Bravo P., Brenna E., Mioskowski C., Panzer W., Viani F., Volonterio A., Wagner A., and Zanda M. Tetrahedron 59 (2003) 7147-7156 The regiochemistry of 7a was also confirmed by NOE study
16. Bis-Boc protection was chosen over Mono-Boc due to the attempted Mono-Boc protection giving a mixture of both products and starting material. In terms of reactivity for the subsequent coupling reaction, Mono-Boc protected 7a showed a comparable reactivity with 10a.
17. 3) δ 5.69 (s, 1H), 4.55 (s, 2H), 3.71-3.66 (m, 4H), 1.64-1.58 (m, 2H), 1.57-1.50 (m, 4H). ESIMS (m/z): 213 (M+H).
18. 3) δ 6.89 (s, 1H), 3.67 (m, 4H), 1.69-1.47 (m, 24H). ESIMS (m/z): 413 (M+H).
19. 1H NMR (600 MHz, DMSO) δ 8.50 (s, 1H), 7.46 (d, J = 7.9 Hz, 2H), 7.18 (t, J = 7.8 Hz, 2H), 6.81 (t, J = 7.3 Hz, 1H), 5.84 (s, 2H), 5.14 (s, 1H), 3.66-3.54 (m, 4H), 1.55 (d, J = 5.1 Hz, 2H), 1.43 (m, 4H). ESIMS (m/z): 270 (M+H).
20. 1H NMR (600 MHz, DMSO) δ 9.22 (s, 1H, NH), 8.89 (s, 1H, NH), 8.22 (s, 1H), 7.72 (dd, J = 1.8, 7.8 Hz, 1H), 7.54 (d, J = 7.2 Hz, 2H), 7.45 (m, 1 H), 7.29 (m, 3H), 6.92 (m, 1H), 5.52 (s, 1H, pyrimidine CH), 3.71 (m, 4H), 1.64 (m, 2H), 1.54 (m, 4H). ESIMS (m/z): 371 (M+H).