Reaktion #1728528

Reaktionsgleichung

water

4-chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxide

(R)-(−)-2-phenylglycinol

diisopropylethylamine

→

(R)-2-{2-[4-(4-CHLORO-PHENYL)-PIPERAZIN-1-YL]-5-OXO-6,7-DIHYDRO-5H-5λ4-THIENO [3,2-D]PYRIMIDIN-4-YLAMINO}-2-PHENYL-ETHANOL

Lösungsmittel

DMSO

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe precipitate formed
2. 2
   Filtrationfiltered
3. 3
   Waschenwashed
4. 4
   Sonstigedried
5. 5
   SonstigeThe diastereomers are separated by preparative HPLC (method B)
6. 6
   Sonstige52.8 mg of Diastereomer 1 (Example 49) and 42.0 mg of Diastereomer 2 (Example 56) are obtained as a powder

Vorschrift

220 mg 4-chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxide (cf Example 124), 157.48 mg (R)-(−)-2-phenylglycinol and 197.52 μl diisopropylethylamine are placed in 4 ml dioxane, heated to 120° C. in the microwave for 0.3 hours. Then the reaction mixture is mixed with water, the precipitate formed is suction filtered, washed and dried. The diastereomers are separated by preparative HPLC (method B). 52.8 mg of Diastereomer 1 (Example 49) and 42.0 mg of Diastereomer 2 (Example 56) are obtained as a powder. 1H NMR (400 MHz, DMSO): Diastereomer 1: 7.41-7.35 (m, 2H), 7.35-7.28 (m, 2H), 7.28-7.19 (m, 3H), 6.99-6.92 (m, 2H); Diastereomer 2: 7.42-7.35 (m, 2H), 7.33-7.15 (m, 5H), 6.99-6.92 (m, 2H).

Quelle