2,4-dichloro-7,8-dihydro-6H-Thiopyrano[3,2-d]pyrimidine synthesis
- Product Name:2,4-dichloro-7,8-dihydro-6H-Thiopyrano[3,2-d]pyrimidine
- CAS Number:87466-23-7
- Molecular formula:C7H6Cl2N2S
- Molecular Weight:221.11
![7,8-dihydro-1H-thiopyrano[3,2-d]pyrimidine-2,4(3H,6H)-dione](/CAS/20180703/GIF/87466-56-6.gif)
87466-56-6
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87466-23-7
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Yield:87466-23-7 82%
Reaction Conditions:
with N,N-dimethyl-aniline;trichlorophosphate at 90; for 18 h;
Steps:
2,4-Dichloro-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine (10)
A solution of 9 (421 mg, 2.29 mmol) and N,N-dimethylaniline (0.070 mL) in phosphoryl chloride (1.0 mL) was stirred at 90 °C for 18 h. After cooling, the reaction mixture was poured into ice water (50 mL) and the mixture was extracted twice with CHCl3 (30 mL). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed (EtOAc/hexane = 0% to 10%) to give the title compound (414 mg, 1.87 mmol, 82%) as a solid. 1H NMR (CDCl3) δ: 2.21-2.28 (2H, m), 2.99 (2H, t, J = 6.3 Hz), 3.09-3.13 (2H, m). MS (ESI) m/z: 221 (M+H)+.
References:
Goto, Taiji;Shiina, Akiko;Murata, Takeshi;Tomii, Masato;Yamazaki, Takanori;Yoshida, Ken-Ichi;Yoshino, Toshiharu;Suzuki, Osamu;Sogawa, Yoshitaka;Mizukami, Kiyoshi;Takagi, Nana;Yoshitomi, Tomomi;Etori, Maki;Tsuchida, Hiroshi;Mikkaichi, Tsuyoshi;Nakao, Naoki;Takahashi, Mizuki;Takahashi, Hisashi;Sasaki, Shigeki [Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,# 3,p. 893 - 899] Location in patent:supporting information
87466-56-6
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87466-23-7
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![7,8-Dihydro-2-(methylthio)-3H-thiopyrano[3,2-d]pyrimidin-4(6H)-one](/CAS/GIF/87466-55-5.gif)
87466-55-5
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87466-23-7
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$472.00/500mg
58509-73-2
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87466-23-7
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38555-40-7
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87466-23-7
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$472.00/500mg