ChemicalBook CAS DataBase List 4-Chloro-6-ethyl-5-fluoropyrimidine

4-Chloro-6-ethyl-5-fluoropyrimidine synthesis

7synthesis methods

Product Name:4-Chloro-6-ethyl-5-fluoropyrimidine
CAS Number:137234-74-3
Molecular formula:C6H6ClFN2
Molecular Weight:160.58

137234-87-8
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$9.00/1g

137234-74-3
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$10.00/1g

Yield:137234-74-3 99%

Reaction Conditions:

with triethylamine;trichlorophosphate in dichloromethane at 48; for 6 h;Product distribution / selectivity;Industry scale;Heating / reflux;

Steps:

2
A reactor was charged with dichloromethane (20 I) and 6-ethyl-5- fluoropyrimidin-4(1 H)-one (5.00 kg, 35.2 mol) at 25-30 ⁰C. The reaction mixture was stirred for 15 min, and triethylamine (3.60 kg, 35.6 mol) was added. Phosphorus oxychloride (5.95 kg, 38.8 mol) was added over 3 h, while the reaction temperature was kept below 35 ⁰C. The reaction mass was heated at reflux (40-48 ⁰C) for 3 h. The mixture was cooled to 5 ⁰C, and hydrochloric acid (3.7 M, 20 I, 74 mol) was added over 1 h. The mixture was stirred for 30 min at 20 ⁰C. The layers were separated, and the aqueous layer was extracted twice with dichloromethane (2 x 5.0 I). The combined organic layers were washed with water (5.0 I), and the solvents were removed at reduced pressure (550 mmHg) at 28-46 ⁰C. 5.61 kg (99% yield) of the title compound was obtained as a brown liquid. Purity, HPLC: 99.6%.

References:

AXELLIA PHARMACEUTICALS APS WO2009/24214, 2009, A1 Location in patent:Page/Page column 3-4

FullText

137234-87-8
232 suppliers
$9.00/1g

137234-74-3
315 suppliers
$10.00/1g

References

188416-35-5 Synthesis