2,4-Dichloro-5-fluoropyrimidine → 2-chloro-N4-[(2,5-dimethyl-3-furyl)methyl]-5-fluoro-4-pyrimidineamine

HRID 405470

Reaktionsgleichung

Reaktionsgleichung von HRID 405470
[CH2:1]1[CH2:10][O:9][C:8]2[CH:7]=C[C:5]([NH:11][C:12]3[C:17]([F:18])=[CH:16][N:15]=[C:14](NC4C=CC=C(O)C=4)[N:13]=3)=[CH:4][C:3]=2O1.CC1OC(C)=CC=1CN.[Cl:36]C1N=C(Cl)C(F)=CN=1>>[Cl:36][C:14]1[N:13]=[C:12]([NH:11][CH2:5][C:4]2[CH:3]=[C:8]([CH3:7])[O:9][C:10]=2[CH3:1])[C:17]([F:18])=[CH:16][N:15]=1

Komponenten

4

Edukt 3

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 2776162(2,5-Dimethylfuran-3-yl)methanamineHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamine

Produkt 1

HCID 220610932-chloro-N4-[(2,5-dimethyl-3-furyl)methyl]-5-fluoro-4-pyrimidineamine

Versuchsvorschrift

In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of (2,5-dimethyl-3-furyl)methylamine (188 mg, 1.5 mmol) and 2,4-dichloro-5-fluoropyrimidine (50 mg, 0.3 mmol) gave 2-chloro-N4-[(2,5-dimethyl-3-furyl)methyl]-5-fluoro-4-pyrimidineamine. The reaction of 2-chloro-N4-[(2,5-dimethyl-3-furyl)methyl]-5-fluoro-4-pyrimidineamine and 3-aminophenol (200 mg, 1.83 mmol) gave N4-[(2,5-dimethyl-3-furyl)methyl]-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine (50 mg, 51%). 1H NMR (CDCl3): δ 2.22 (s, 3H), 2.23 (s, 3H), 4.39 (d, J=5.1 Hz, 2H), 5.24 (br, 1H), 5.90 (s, 1H), 6.52 (d, J=6.6 Hz, 1H), 6.99 (d, J=8.1 Hz, 1H), 7.13 (t, J=8.1 Hz, 1H), 7.29 (s, 1H), 7.71 (m, 2H); 19F NMR (282 MHz, CDCl3): δ −167.84; LCMS: ret. time: 19.83 min.; purity: 96.32%; MS (m/e): 329.05 (MH+).

Quellen und Nachweise

ORD-Eintrag
ord-2456ba25fa574d5f99e391b625419429
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748597B2

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