2,4-Dichloro-5-fluoropyrimidine → 2-chloro-N4-(3,5-dimethyl-4-methoxyphenyl)-5-fluoro-4-pyrimidineamine

HRID 71477

Reaktionsgleichung

Reaktionsgleichung von HRID 71477
C1COC2C=CC(NC3C(F)=CN=C(NC4C=CC=C(O)C=4)N=3)=CC=2O1.[CH3:27][C:28]1[CH:29]=[C:30]([CH:32]=[C:33]([CH3:37])[C:34]=1[O:35][CH3:36])[NH2:31].[Cl:38][C:39]1[N:44]=[C:43](Cl)[C:42]([F:46])=[CH:41][N:40]=1>>[Cl:38][C:39]1[N:44]=[C:43]([NH:31][C:30]2[CH:32]=[C:33]([CH3:37])[C:34]([O:35][CH3:36])=[C:28]([CH3:27])[CH:29]=2)[C:42]([F:46])=[CH:41][N:40]=1

Komponenten

4

Edukt 3

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 41660974-Methoxy-3,5-dimethylanilineHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamine

Produkt 1

HCID 220611692-chloro-N4-(3,5-dimethyl-4-methoxyphenyl)-5-fluoro-4-pyrimidineamine

Versuchsvorschrift

In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-N2-(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, the reaction of 3,5-dimethyl-4-methoxyaniline (400 mg, 2.6 mmol) and 2,4-dichloro-5-fluoropyrimidine (200 mg, 1.2 mmol) gave 2-chloro-N4-(3,5-dimethyl-4-methoxyphenyl)-5-fluoro-4-pyrimidineamine. The reaction of 2-chloro-N4-(3,5-dimethyl-4-methoxyphenyl)-5-fluoro-4-pyrimidineamine and 3-(methoxycarbonylmethyleneoxy)aniline (650 mg, 3.6 mmol) gave N4-(3,5-dimethyl-4-methoxyphenyl)-5-fluoro-N2-(3-methoxycarbonylmethyleneoxyphenyl)-2,4-pyrimidinediamine (180 mg, 35%). 1H NMR (CD3OD): δ 2.20 (s, 6H), 3.70 (s, 3H), 3.74 (s, 3H), 4.52 (s, 2H), 6.76 (ddd, J=0.9, 2.4 and 8.4 Hz, 1H), 7.03-7.08 (m, 2H), 7.24 (m, 3H), 7.96 (d, J=5.4 Hz, 1H); 19F NMR (282 MHz, CD3OD): δ−162.92; LCMS: ret. time: 23.13 min.; purity: 100%; MS (m/e): 427.04 (MH+).

Quellen und Nachweise

ORD-Eintrag
ord-78bb4f325eff4100901e62616bcaeb74
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822685B2

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