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18162-48-6872-50-4Methylene ChloridenaphthaleneTHFTitanium Dioxide
ChemicalBook CAS DataBase List 4-[6-Chloro-2-(2-(pyridin-2-yl)ethoxy)pyriMidin-4-yl]Morpholine
544693-01-8

4-[6-Chloro-2-(2-(pyridin-2-yl)ethoxy)pyriMidin-4-yl]Morpholine synthesis

2synthesis methods
2-(2-Hydroxyethyl)pyridine

103-74-2
367 suppliers
$8.00/10g

10397-13-4 Synthesis
4-(4,6-Dichloropyrimidin-2-yl)morpholine

10397-13-4
163 suppliers
$11.00/250mg

4-(2,6-DICHLOROPYRIMIDIN-4-YL)MORPHOLINE

52127-83-0
70 suppliers
$95.00/1g

4-[6-Chloro-2-(2-(pyridin-2-yl)ethoxy)pyriMidin-4-yl]Morpholine

544693-01-8
10 suppliers
$165.00/100mg

Morpholine, 4-[2-chloro-6-[2-(2-pyridinyl)ethoxy]-4-pyrimidinyl]-

887402-10-0
0 suppliers
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Morpholine, 4-[4-chloro-6-[2-(2-pyridinyl)ethoxy]-2-pyrimidinyl]-

887402-09-7
0 suppliers
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Yield:544693-01-8 88%

Reaction Conditions:

with sodium hydride in N,N-dimethyl-formamide;oil at 0 - 5; for 0.5 h;

Steps:

1.2

Step 2.Product 1 (114.7g, 0.49 mol) and 2-(2-hydroxyethyl)-pyridine, 98% (64.66 g, 0.514 mol) were dissolved in anhydrous DMF (539 mL) and cooled to 0 0C. Sodium hydride, 60% dispersion in oil, (23.52 g, 0.588 mol) was added under nitrogen purge to the vigorously stirred reaction mixture in 6 portions, to maintain the reaction temperature below 5 0C. The EPO reaction was stirred for 30 minutes, then checked by TLC to determine completion of the reaction. When the reaction was complete, heptane (107.7 mL, 0.735 mol) was added, and the reaction was allowed to stir for additional 1.5 hours at room temperature before it was carefully quenched with ice water (539 mL) and left overnight for precipitation to be completed. The precipitated solid was filtered out, washed 3 times with water (245 mL per wash), then 3 times with heptane (98 mL per wash), and vacuum-dried at 40-50 0C until constant weight was maintained to yield Product 2 (97.4 g, 62% yield) as a mixture of regioisomers. Product 2 contained the desired regioisomer, 2-[2-(pyridin-2-yl)-ethoxy]-4- chloro-6-(moφholin-4-yl)-pyrimidine (88%), as well as 4-[2-(pyridm-2-yl)-ethoxy]-6- chloro-2-(morpholin-4-yl)-pyrimidine and 6-[2-(pyridin-2-yl)-ethoxy]-2-chloro-4-(morpholin-4-yl)-pyrimidine which together made up less than 12%.

References:

WO2006/53112,2006,A1 Location in patent:Page/Page column 51-52

2-(2-Hydroxyethyl)pyridine

103-74-2
367 suppliers
$8.00/10g

4-(2,6-DICHLOROPYRIMIDIN-4-YL)MORPHOLINE

52127-83-0
70 suppliers
$95.00/1g

4-[6-Chloro-2-(2-(pyridin-2-yl)ethoxy)pyriMidin-4-yl]Morpholine

544693-01-8
10 suppliers
$165.00/100mg

References