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CAS No. : | 5018-38-2 | MDL No. : | MFCD00087680 |
Formula : | C5H4Cl2N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IJQIGKLDBGKSNT-UHFFFAOYSA-N |
M.W : | 179.00 | Pubchem ID : | 78720 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In dimethyl sulfoxide; at 60℃;Product distribution / selectivity; | Example 1(6-Chloro-5-methoxy-pyrimidin-4-yl)-(6-methanesulfonyl-2-methyl-pyridin-3-yl)-amine A 100-mL Schlenk flask with a magnetic stir bar was charged with 4,6-dichloro-5-methoxypyrimidine (4.66 g, 0.026 mol), <strong>[897732-75-1]6-methanesulfonyl-2-methyl-3-pyridinamine</strong> (3.72 g, 0.020 mol), and DMSO (20 mL). After the mixture was stirred to dissolve the components, Cs2CO3 (8.48 g, 0.026 mol) was added, and the resulting mixture heated to 60 C. After 4.5 h and additional portion of Cs2CO3 (2.00 g, 0.0061 mol) was added and heating continued overnight. The reaction was quenched by addition of the reaction mixture to well stirred, saturated NH4Cl (200 mL); resulting in the formation of a tan precipitate. The precipitate was filtered, air dried and stirred with MTBE, and the resulting mixture filtered again. The resulting solid was purified by column chromatography on silica gel (200 g) using CH2Cl2 followed by 1% IPA-CH2Cl2 after 2-L of CH2Cl2 had eluted to yield the title compound as a white to light yellow solid.1H NMR (300 MHz, CDCl3) delta: 8.99 (d, 1H, J=8.6 Hz), 8.37 (s, 1H), 8.00 (d, 1H, J=8.6 Hz), 7.49 (br s, 1H), 4.08 (s, 3H), 3.21 (s, 3H), 2.69 (s, 3H).HRMS: [MH]+ m/z=329.0465.NOTE: (6-Chloro-5-methoxy-pyrimidin-4-yl)-(6-methanesulfonyl-2-methyl-pyridin-3-yl)-methyl-amine was also isolated as a by-product from the above reaction mixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.07 g | With potassium tert-butylate; In tetrahydrofuran; at 0 - 20℃; for 1.0h; | Potassium 2-niethylpropan-2-olate (17.3 niL, 17.3 mmol) was added to a solution of 1- (4-(irifiuoromethyl)pyrimidin-2--yl)piperidin-4-ol (3.89 g, 15.7 mmoi) and 4,6-dichioro--5- methoxypyrimidinc (2.82 g, 15.7 mmol) in THF (58 mL) at 0 C. The reaction was warmed toroom temperature and stirred fOr I Iv The reaction was concentrated to a yellow solid and triturated with EtOAc and hexanes to afford 6.07 g of the tide compound. Exact mass calculated for C,1H,5CIF,N501?. 38909, found: LCMS rn/a = 390.4 [M+H]?; ?H NMR (400 MHz, CDCI3) S ppm I .86-1.96 (m, 2H), 2,08-2,17 (in, 21-1), 3.75-3.84 (in. 2Fl), 3.92 (s, 3H), 4.21-4.29 (m. 21-1), 5.50 (septet, J= 3.8 Fiz, 11-1). 6.77 (d, .J= 4,8 1-lz, lFl). 8.29 (s, 11-1), 8,50 (d,,J= 4.8 Flz, 1H). |
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