2,4-Dichloro-5-fluoropyrimidine → 2-chloro-5-fluoro-N4-[2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one-6-yl]-4-pyrimidineamine

HRID 603570

Reaktionsgleichung

Reaktionsgleichung von HRID 603570
ClC1N=C(NC2C=CC3OCCOC=3C=2)C(F)=CN=1.[Cl:20][C:21]1[N:26]=[C:25](Cl)[C:24]([F:28])=[CH:23][N:22]=1.[NH2:29][C:30]1[CH:31]=[CH:32][C:33]2[O:34][CH2:35][C:36](=[O:40])[NH:37][C:38]=2[N:39]=1>>[Cl:20][C:21]1[N:26]=[C:25]([NH:29][C:30]2[CH:31]=[CH:32][C:33]3[O:34][CH2:35][C:36](=[O:40])[NH:37][C:38]=3[N:39]=2)[C:24]([F:28])=[CH:23][N:22]=1

Komponenten

4

Edukt 3

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 220603622-chloro-5-fluoro-N-(3,4-ethylenedioxyphenyl)-4-pyrimidineamineHCID 220605636-amino-2H,3H,4H-pyrido[3,2-b][1,4]oxazin-3-one

Produkt 1

HCID 220604032-chloro-5-fluoro-N4-[2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one-6-yl]-4-pyrimidineamine

Versuchsvorschrift

In a manner similar to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 6-amino-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one were reacted to yield 2-chloro-5-fluoro-N4-[2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one-6-yl]-4-pyrimidineamine. 1H NMR (DMSO-d6): δ 4.63 (s, 2H), 7.34 (d, J=8.7 Hz, 1H), 7.44 (d, J=8.4 Hz, 1H), 8.33 (d, J=3.3 Hz, 1H), 10.14 (s, 1H, NH), 11.19 (s, 1H, NH); 19F NMR (282 MHz, DMSO-d6): 6-152.35; LCMS: ret. time: 26.74 min.; purity: 85.90%; MS (m/e): 296.13 (MH+).

Aufarbeitung

  1. customwere reacted

Quellen und Nachweise

ORD-Eintrag
ord-e3de06c268d94aea901fbc756f5d9a9f
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906644B2

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