1,4-Benzodioxan-6-ylamine → N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-hydro xy-2-phenylethyl)-2,4-pyrimidinediamine

HRID 71433

Reaktionsgleichung

Reaktionsgleichung von HRID 71433
C1COC2C=CC([NH:11][C:12]3[C:17]([F:18])=[CH:16][N:15]=[C:14]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=4)[N:13]=3)=CC=2O1.ClC1N=C(N[CH2:35][CH:36]([OH:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)C(F)=CN=1.[CH2:45]1[CH2:55]OC2C=CC(N)=CC=2[O:46]1>>[CH2:55]1[CH2:45][O:46][C:23]2[CH:24]=[CH:25][C:20]([N:19]([CH2:35][CH:36]([OH:43])[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:14]3[N:13]=[C:12]([NH2:11])[C:17]([F:18])=[CH:16][N:15]=3)=[CH:21][C:22]=2[O:26]1

Komponenten

4

Edukt 3

HCID 891481,4-Benzodioxan-6-ylamineHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamineHCID 220608272-chloro-5-fluoro-N4-(2-hydroxy-2-phenylethyl)-4-pyrimidineamine

Produkt 1

HCID 22060669N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-hydro xy-2-phenylethyl)-2,4-pyrimidinediamine

Versuchsvorschrift

In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(2-hydroxy-2-phenylethyl)-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to yield N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-hydroxy-2-phenylethyl)-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.79 (s, 1H), 7.48 (m, 5H), 6.89-6.71 (m, 3H), 5.41-5.38, 4.97 (dd, 1H, J=3.6 and 7.5 Hz), 4.28-4.22 (m, 4H), 3.88 (ddd, 1H, J=4.2, 7.2, and 14.1), 3.64-3.55 (m, 1H); 19F NMR (CDCl3): −47910; LCMS: ret. time: 20.47 min.; purity: 88%; MS (m/e): 383 (MH+).

Aufarbeitung

  1. customwere reacted

Quellen und Nachweise

ORD-Eintrag
ord-ff845071e59c48b1a0ca45a20b43c0cd
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822685B2

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