2-Chloroethyl isocyanate → 1-(2-Chloroethyl)-3-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)urea

HRID 446341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446341
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[N:14]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[C:4]([CH3:23])[CH:3]=1.[Cl:24][CH2:25][CH2:26][N:27]=[C:28]=[O:29]>C1COCC1>[Cl:24][CH2:25][CH2:26][NH:27][C:28]([NH:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[N:14]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[C:4]([CH3:23])[CH:3]=1)=[O:29]

Komponenten

4

Edukt 2

HCID 160352-Chloroethyl isocyanateHCID 469295424-(2-(4-amino-2-methylphenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine

Produkt 1

HCID 669705851-(2-Chloroethyl)-3-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a slurry of 4-(2-(4-amino-2-methylphenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine (0.500 g, 1.63 mmol) in THF (3.3 mL) under nitrogen was added 1-chloro-2-isocyanatoethane (0.157 mL, 1.79 mmol). The reaction became clear and brown, and then a precipitate formed. Additional THF (4 mL) was added to promote stirring, and the reaction was allowed to stir for 16 h. The mixture was filtered, the solid was rinsed with diethyl ether, and dried in vacuo to give 1-(2-chloroethyl)-3-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)urea as a tan solid. MS m/z=413 [M+1]+. Calc'd for C20H21ClN6O2: 412.14.

Aufarbeitung

  1. custombrown, and then a precipitate formed
  2. stirringto stir for 16 h
  3. filtrationThe mixture was filtered
  4. washthe solid was rinsed with diethyl ether
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7b5f4367d0454ce48ccbc11763d0d525
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476434B2

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