4-Chloro-2-methylthiopyrimidine → 1-(2-Methylsulfanyl-pyrimidin-4-yl)-7-phenyl-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one

HRID 1785465

Reaktionsgleichung

Reaktionsgleichung von HRID 1785465
[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14]C[CH2:12][N:11]3[C:15](=[O:25])[CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:18]=[C:10]23)[CH:6]=[CH:5][N:4]=1.C1(C2C=C3NCCN3C(=O)C=2)C=CC=CC=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.ClC1C=CN=C(SC)N=1>C1(C)C=CC=CC=1>[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:10]3=[CH:18][C:17]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:16][C:15](=[O:25])[N:11]3[CH2:12][CH2:14]2)[CH:6]=[CH:5][N:4]=1

Komponenten

7

Edukt 5

HCID 971134-Chloro-2-methylthiopyrimidineHCID 634876Binap, (A+-)-HCID 3050276Imidazo(1,2-a)pyridin-5(1H)-one, 2,3-dihydro-7-phenyl-HCID 23676156Sodium t-butoxideHCID 575931211-(2-Methylsulfanyl-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one

Produkt 1

HCID 575931601-(2-Methylsulfanyl-pyrimidin-4-yl)-7-phenyl-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Following the procedure described for the synthesis of 1-(2-methylsulfanyl-pyrimidin -4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one, but using 7-phenyl-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one (1 g, 4.7 mmol), sodium tert-butoxide (1.26 g, 13.16 mmol), BINAP (0.43 g, 0.7 mmol), Pd (OAc)2 (0.16 g, 0.7 mmol), toluene (20 mL) and 4-chloro-2-methylthiopyrimidine (0.66 mL, 0.56 mmol). The title compound was isolated as a yellow solid. MS m/e 337 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-18463e1b15a84f3184de7f73294a6b77
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504403B2

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