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Hydrochloric Acid → 4-(2-(4-MorpholinophenylaMino)pyriMidin-4-yl)benzoic acid

HRID 589569
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 589569
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[C:18]([C:20]4[CH:30]=[CH:29][C:23]([C:24]([O:26]CC)=[O:25])=[CH:22][CH:21]=4)[CH:17]=[CH:16][N:15]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.CO.O1CCCC1.[OH-].[Li+].Cl>O>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[C:18]([C:20]4[CH:30]=[CH:29][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=4)[CH:17]=[CH:16][N:15]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 25062762ethyl 4-(2-(4-MorpholinophenylaMino)pyriMidin-4-yl)benzoate

Produkt 1

HCID 579908204-(2-(4-MorpholinophenylaMino)pyriMidin-4-yl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

A solution of ethyl 4-(2-(4-morpholinophenylamino)pyrimidin-4-yl)benzoate (35.39 g, 87.6 mmol) in 3:1 methanol/tetrahydrofuran (350 mL) was treated with lithium hydroxide (4.41 g, 183.9 mmol) in water (90 mL). The mixture was heated at reflux for 2 h., cooled, concentrated and acidified with hydrochloric acid (2M, 92.5 mL, 185 mmol). The dark precipitate was filtered, washed with water, and dried under vacuum. The solid was ground to a powder with a mortar and pestle, triturated with methanol (500 mL) then filtered again to yield 4-(2-(4-morpholinophenylamino)pyrimidin-4-yl)benzoic acid as a muddy solid. This material was washed with ether, air dried overnight, and ground to a fine powder with mortar and pestle. On the basis of mass recovery (34.49 g) the yield was assumed to be quantitative. 1H NMR (300 MHz, d6-DMSO) δ 9.47 (1H, s); 8.53 (1H, d, J=5.2 Hz); 8.24 (2H, d, J=8.5 Hz); 8.08 (2H, d, J=8.8 Hz), 7.66 (2H, d, J=9.1 Hz); 7.37 (1H, d, J=5.2Hz); 6.93 (2H, d, J=9.1 Hz); 3.73 (4H, m); 3.04 (4H, m). LC-ESI-MS (method C): rt 7.3 min.; m/z 377.1 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h.
  3. temperaturecooled
  4. concentrationconcentrated
  5. filtrationThe dark precipitate was filtered
  6. washwashed with water
  7. customdried under vacuum
  8. customtriturated with methanol (500 mL)
  9. filtrationthen filtered again

Quellen und Nachweise

ORD-Eintrag
ord-462c60c492094a73be5b567686e6748f
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09233934B2

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