Lithium Hydroxide → HCID 59618129, Verbindung

HRID 449938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449938
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:3]=1[C:4]([NH:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=2)[CH:8]=1)=[O:5].[Li+].[OH-]>C1COCC1>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:3]=1[C:4]([NH:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:24]=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)[CH:8]=1)=[O:5]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 59618316HCID 59618316, Verbindung

Produkt 1

HCID 59618129HCID 59618129, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of ethyl 4-(6-(2,6-dichlorobenzamido)pyrimidin-4-ylamino)benzoate (0.279 g, 0.647 mmol) in THF (5 mL) was added a solution of 3 N LiOH (2 mL). The mixture was heated at 60° C. for 12 hrs. THF was removed under reduced pressure. The residue was diluted with water, acidified with 1 N HCl to pH 3.0. The precipitated white solid was collected by filtration, washed with water, dried in high vacuum to give 4-(6-(2,6-dichlorobenzamido)pyrimidin-4-ylamino)benzoic acid (0.24 g, yield: 92%). 1H NMR (500 MHz, DMSO) δ 12.52 (s, 1H), 11.41 (s, 1H), 10.07 (s, 1H), 8.53 (s, 1H), 7.90 (d, J=8.9 Hz, 2H), 7.85 (d, J=8.9 Hz, 2H), 7.78 (d, J=0.8 Hz, 1H), 7.58-7.53 (m, 2H), 7.49 (dd, J=9.1, 6.9 Hz, 1H). LCMS (ESI) m/z: 403.0 [M+H+].

Aufarbeitung

  1. customTHF was removed under reduced pressure
  2. additionThe residue was diluted with water
  3. filtrationThe precipitated white solid was collected by filtration
  4. washwashed with water
  5. customdried in high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-48a7fed144eb4deab421dc6780dd20ce
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486950B2

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