2-Aminopyrimidine → 6-Chloro-2-methyl-4-(pyrimidin-4-ylamino)pyridazin-3(2H)-one

HRID 872152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872152
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:19]=[C:13]3CN(C)C[CH2:17][N:12]3[N:11]=2)[C:5](=[O:8])[NH:6][N:7]=1.N[C:21]1N=CC=CN=1.BrC1C(=O)N(C)N=C(Cl)C=1>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:19]=[CH:13][N:12]=[CH:17][N:11]=2)[C:5](=[O:8])[N:6]([CH3:21])[N:7]=1

Komponenten

4

Edukt 3

HCID 79782-AminopyrimidineHCID 585403166-chloro-4-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridazin-3(2H)-oneHCID 592164744-Bromo-6-chloro-2-methyl-2,3-dihydropyridazin-3-one

Produkt 1

HCID 666102376-Chloro-2-methyl-4-(pyrimidin-4-ylamino)pyridazin-3(2H)-oneAusbeute 69 %

Versuchsvorschrift

Using the same general procedure as described for the preparation of 101m, reaction of 2-aminopyrimidine (450 mg, 4.74 mmol) with 103a (1.06 g, 4.74 mmol) afforded 103b in 69% yield (745 mg) as an amorphous yellow solid: mp 233-235° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.05 (s, 1H), 8.92 (d, J=1.0 Hz, 1H), 8.54 (d, J=5.5 Hz, 1H), 8.45 (s, 1H), 7.58 (dd, J=6.0, 1.0 Hz, 1H), 3.70 (s, 3H); MS (ESI+) m/z 238.0 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-736cc5ecd6ec451e923a3bbf3b35c2f8
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975260B2

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