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CAS No. : | 1111638-74-4 | MDL No. : | MFCD12756165 |
Formula : | C8H7IN4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XBRURAHDFBJPMJ-UHFFFAOYSA-N |
M.W : | 318.14 | Pubchem ID : | 46864160 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-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 |
---|---|---|
54.6% | Stage #1: With sulfuric acid; iodine; acetic acid; potassium iodide; sodium nitrite In water at -3 - 50℃; for 2 h; |
Preparation of 4-(5-iodo-1 H-pyrazol-4-yl)-2-(methylthio)pyrimidine (A)A solution of NaNO2 (20.0 g, 0.29 mol) in water (150 mL) was poured into a solution of 4-(2- (methylthio)pyrimidin-4-yl)-1 H-pyrazol-5-amine 6 (50.0 g, 0.24 mol) in a mixture of glacial acetic acid (400 mL) and water (100 mL) at -3 0C. The temperature increased to -1 0C. Concentrated H2SO4 (10 mL) was added to the obtained solution, and a solution of potassium iodide (120.0 g, 1.2 mol.) and I2 (123.0 g, 10.48 mol) in water (200 mL) was added dropwise. The obtained solution was heated to 50 0C for 2 h, and the mixture was neutralized with aqueous ammonia. Excess iodine was treated with Na2S2O3. The precipitate was filtered, and the filtrate was extracted with ethyl acetate. The organic layer was evaporated, and the residue was purified by chromatography (THF: EtOAc = 4:1 ) to give 4-(5-iodo-1 H- pyrazol-4-yl)-2-(methylthio)pyrimidine (A) (42.2 g, 54.6percent) as a yellow solid. 1H NMR (400 MHz, DMSO): δ 8.55 (d, 1 H), 8.35 (s, 1H), 7.55 (d, 1 H), 2.55 (s, 3H). |
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