2-Pyrimidinamine, 5-bromo-N,N-bis[(4-methoxyphenyl)methyl]- synthesis
- Product Name:2-Pyrimidinamine, 5-bromo-N,N-bis[(4-methoxyphenyl)methyl]-
- CAS Number:1272403-00-5
- Molecular formula:C20H20BrN3O2
- Molecular Weight:414.3
7752-82-1
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Yield:1272403-00-5 92%
Reaction Conditions:
Stage #1: 5-bromo-pyrimidin-2-ylaminewith sodium hydride;sodium iodide in N,N-dimethyl-formamide;mineral oil at 0; for 0.25 h;
Stage #2: p-methoxybenzyl chloride in N,N-dimethyl-formamide;mineral oil at 0 - 20; for 0.5 h;
Steps:
5.1.6 5.1.6. 5-Bromo-N,N-bis[(4-methoxyphenyl)methyl]pyrimidin-2-amine (13)
To a suspension of 5-bromopyrimidin-2-amine (5.00 g, 28.7 mmol) and NaI (431 mg, 2.87 mmol) in DMF (60 ml) was added NaH (60% dispersion in mineral oil, 2.87 g, 71.8 mmol) at 0 °C.
After stirring for 15 min at 0 °C, 1-(chloromethyl)-4-methoxy-benzene (8.57 ml, 63.2 mmol) was added at 0 °C.
After stirring for 30 min at ambient temperature, the reaction mixture was neutralized by saturated aqueous NH4Cl.
The resulting mixture was extracted with EtOAc.
The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure.
The residue was purified by flash column chromatography (n-hexane/EtOAc, 1/0 to 9/1) to afford the titled compound as a white solid (10.9 g, 92%).
1H NMR (400 MHz, DMSO-d6) δ: 8.49 (2H, s), 7.16 (4H, d, J = 8.8 Hz), 6.87 (4H, d, J = 8.8 Hz), 4.68 (4H, s), 3.72 (6H, s); HRMS (ESI), m/z calcd for C20H20BrN3O2 + H: 414.0817, found 414.0814.
References:
Kawada, Hatsuo;Ebiike, Hirosato;Tsukazaki, Masao;Yamamoto, Shun;Koyama, Kohei;Nakamura, Mitsuaki;Morikami, Kenji;Yoshinari, Kiyoshi;Yoshida, Miyuki;Ogawa, Kotaro;Shinma, Nobuo;Tsukuda, Takuo;Ohwada, Jun [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 24,p. 7650 - 7660]
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