(5-BroMo-2-chloro-pyriMidin-4-yl)-Methyl-aMine synthesis

Yield:205672-24-8 100%

Reaction Conditions:

in methanol at 0 - 20; for 3.66667 h;

Steps:

1 5.1.1 5-Bromo-2-chloro-N-methyl-pyrimidin-4-amine (3a)

Methylamine (9.8 M MeOH solution) (8.9 ml, 87.7 mmol) was added dropwise at 0 °C over 20 min to a solution of 5-bromo-2,4-dichloropyrimidine (10 g, 43.9 mmol) in MeOH (150 ml). After stirring for 20 min at 0 °C, the mixture was warmed to room temperature, stirred for 3 h, and evaporated down. The residue was suspended in EtOAc, washed with satd NaHCO₃ and brine, dried with MgSO₄, and evaporated down. The residue was chromatographed on silica gel column to give 10 g of 3a in quantitative yield. R_f = 0.15 (n-hexane/EtOAc = 5:1). ¹H NMR (600 MHz, CDCl₃): δ 8.12 (s, 1H), 5.58 (br s, 1H), 3.10 (d, J = 4.8 Hz, 3H).

References:

Teno, Naoki;Gohda, Keigo;Wanaka, Keiko;Tsuda, Yuko;Sueda, Takuya;Yamashita, Yukiko;Otsubo, Tadamune [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 7,p. 2339 - 2352]