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CAS No. : | 42972-46-3 | MDL No. : | MFCD11553496 |
Formula : | C8H9NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DIASEPULVQSMAS-UHFFFAOYSA-N |
M.W : | 135.16 | Pubchem ID : | 577569 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 potassium carbonate; In water; at 20℃; for 2.5h; | Potassium carbonate (1.97 g, 14.26mmol) was portionwise added to a cold solution of glyoxylic acid (0.548 g, 7.4mmol) in water (10 mL) and the title compound from Preparation 78 (1 g, 7.4 mmole) was slowly incorporated. The mixture was stirred at room temperature for 2.5 hours and then cooled in ice. Acetic acid (3ml, 51.8mmol) was added, followed by hydrazine monohydrate (0.43 mL, 8.9mmol). The solution was heated under reflux for 2 hours and cooled in ice. The pH was adjusted to 7 by the addition of saturated aq. sodium bicarbonate and the solid obtained filtered, washed with cold water, diethyl ether and dried under vacuum to yield a orange solid (0.69 g, 50 %) which was used in the next step without further purification. 8 (DMSO-d6): 2.40 (s, 3H), 7.05 (d,1H), 8.10 (d, 2H), 8.50 (bs,1H), 8.90 (d, 1H). LRMS (m/z): 188 (M+1) +. Retention Time: 4.57 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In diethyl ether; at 0 - 20℃; for 6.0h; | To an ice-cooled suspension of the title compound of Preparation 77 (2.67 g, 14.8 mmole), methyl magnesium bromide (3M in diethyl ether, 9.86 mL) was dropwise added under argon. After the addition was completed, the reaction mixture was stirred at 0 C for one hour and the temperature was then allowed to rise to room temperature and stirred for five additional hours. After this period of time, the reaction was poured into ice, brine was added and the aqueous phase extracted with EtOAc, dried and concentrated to afford a yellowish oil (1.81 g, 91 %) which was used in the next step without further purification. (CDCI3) : 2.40 (s, 3H), 2.65 (s, 3H), 8.05 (bs, 1 H), 8.62 (d,1 H), 8.98 (d, 1H). LRMS (m/z): 136(M+1) +. Retention Time: 4.77 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 80℃; for 1.0h;Microwave irradiation; | Example 12; To a solution of l-(5-methylpyridin-3-yl)ethanone (135 mg, 1 mmol) and N-[(15)-l-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine (248 mg, 1 mmol) in 1,2-dichloroethane (5 mL) was added sodium triacetoxyborohydride (300 mg, 1.4 mmol), in one portion, and glacial acetic acid (0.18 mL, 3 mmol). The mixture was heated in the microwave reactor at 800C for 1 hour. After this time the mixture was stirred with dilute aqueous hydrochloric acid (2M, 7 mL) for 15 minutes and the two phases were separated. The aqueous phase was basified to pH 9 with solid potassium hydroxide and was extracted with dichloromethane (2 x 20 mL). The extracts were washed with brine (20 mL), dried (MgSθ4) and concentrated under reduced pressure to give an orange oil which was purified by flash chromatography (silica, ethyl acetate/methanol) to give6-chloro-N-[( 1 S)- 1 -(3 - { [ 1 -(3-methy lpheny l)ethy l]amino} pheny l)ethy l]pyrazin-2 -amine (52 mg, 14%) as a pale yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | In tetrahydrofuran; diethyl ether; for 2.0h;Heating / reflux; | Synthesis of N-(2-methyl-5-nitrophenyl)-4-(5-methylpyridin-3-yl)pyrimidin-2-amine 21; 5-Methyl-nicotinonitrile (2.08 g, 17.6 mmol) is heated at reflux in dry THF (20 mL) with MgMeBr (3 M solution in Et2O, 10 mL, 30 mmol) for 2 h. After cooling down, aq. Na2CO3 is added slowly to quench the reaction. Extractions with DCM affords the crude <n="33"/>mixture which is purified by silica gel chromatography to yield l-(5-methyl-pyridin-3-yl)- ethanone 18 (0.7 g, 30 %). LC/MS (m/z) (M+l)+: 136.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To 3-bromo-5-methylpyridine 1-1 (2 g, 11.63 mmol) in diethyl ether (30 ml) at -78 C was added uLi (8.72 ml, 13.95 mmol) dropwise. After 30 min, N-methoxy-N- methylacetamide n-BuLi was added. The resulting mixture was stirred at -78 C for 2 h then at rt overnight, quenched with saturated NH4CI solution and diluted with EtOAc. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give a yellow residue, which was purified by column chromatography (0-65% EtOAc in hexane) to give the desired product 1-2: 1H NMR (400 MHz, CDCI3) δ 8.98 (s, IH), 8.62 (s, IH), 8.04 (s, IH), 2.63 (s, 3H)5 2.41 (s, 3H). |
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