60025-05-0|1-(4,6-Dichloropyrimidin-5-yl)ethanol| Ambeed

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CAS No. :	60025-05-0
Formula :	C₆H₆Cl₂N₂O
M.W :	193.03
SMILES Code :	CC(O)C1=C(Cl)N=CN=C1Cl
MDL No. :	MFCD27926144

Yield	Reaction Conditions	Operation in experiment
93%	With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; for 1.58333h;Inert atmosphere;	Step 2.1-(4,6-Dichloro-pyrimidin-5-yl)-ethanone; 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane; 1.3 g, 3.1 mmol) was added to a solution of 1-(4,6-dichloro-pyrimidin-5-yl)-ethanol (from Step 1; 540 mg, 2.8 mmol) in dichloromethane at 0 C. under nitrogen. The reaction mixture was stirred at 0 C. for 5 min and then at room temperature for 90 min. Saturated aqueous sodium bicarbonate solution was added and the mixture was extracted with dichloromethane (3×50 mL). The organic layers were washed with water and brine, dried (sodium sulfate), filtered, and evaporated. The residue was triturated twice with ether/petroleum ether (2:1), the solvent was decanted and the solvent was evaporated to give 1-(4,6-dichloro-pyrimidin-5-yl)-ethanone (500 mg, 93%) which was used directly in the next step without further purification. 1H NMR (300 MHz, CDCl3) delta 2.64 (s, 3H), 8.83 (s, 1H).
86%	With chromium(VI) oxide; In acetone; for 2.5h;	A solution of 1-(4,6-dichloropyrimidin-5-yl)ethanol (8.95 g, 46.4 mmol) in 140 mL of acetone was treated with chromium trioxide (9.27 g, 92.7 mmol). After stirring for 2.5 h, the mixture was quenched with 15 mL of isopropanol and stirred 15 min. The mixture was poured slowly into 500 mL of saturated sodium bicarbonate at O0C. The mixture was extracted 3X with dichloromethane. The combined organics were dried with sodium sulfate to give 8.02 g of material. Chromatography on silica gel, eluting with 10% ethyl acetate / hexanes gave 7.62 g (86%) of 1-(4,6-dichloropyrimidin-5-yl)ethanone; HPLC TR 4.92 min (HPLC Conditions H).
85%	With chromium(VI) oxide; In acetone; at 20℃; for 2h;	980 mg (5.08 mmol) of 1-(4,6-dichloropyrimidine-5-yl)ethane-1-ol prepared in step 2 was dissolved in 30 mL of acetone, to which 1.0 g (10.2 mmol, 2.0 eq) of chromium trioxide was slowly added, followed by stirring at room temperature for 2 hours. 2 mL of Isopropylalcohol was added thereto, followed by stirring for 10 minutes. 20 mL of saturated sodiumbicarbonate aqueous solution was added to the reaction mixture, followed by extraction with ethylacetate. The extracted organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was separated by column chromatography (SiO2, eluent: hexane/ethylacetate, 6/1) to give 823 mg of the target compound 1-(4,6-dichloropyrimidine-5-yl)ethane-1-one as a white solid (4.3 mmol, yield: 85%). 1H NMR(300 MHz, CDCl3) delta 8.84 (s, 1H) , 2.63 (s, 3H).

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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 60025-05-0

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CAS No.: 60025-05-0

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