Sodium Hydroxide → 4-((1S,2S)-2-hydroxycyclopentylamino)-2-(methylthio)pyrimidine-5-carboxylic acid

HRID 2280690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2280690
[OH:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8]1[C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][N:11]=[C:10]([S:19][CH3:20])[N:9]=1.[OH-].[Na+]>C(O)C>[OH:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8]1[C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=[C:10]([S:19][CH3:20])[N:9]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 70982005ethyl 4-((1S,2S)-2-hydroxycyclopentylamino)-2-(methylthio)pyrimidine-5-carboxylate

Produkt 1

HCID 712371554-((1S,2S)-2-hydroxycyclopentylamino)-2-(methylthio)pyrimidine-5-carboxylic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-((1S,2S)-2-hydroxycyclopentylamino)-2-(methylthio)pyrimidine-5-carboxylate (1.3 g, 4.37 mmol) in ethanol (15 mL) was added aqueous sodium hydroxide solution (15 mL, 2 N), and the mixture was stirred for 1 h at room temperature. When the starting material was consumed, the reaction mixture was neutralized with saturated aqueous citric acid solution. The solids were collected by filtration and dried to give 4-((1S,2S)-2-hydroxycyclopentylamino)-2-(methylthio)pyrimidine-5-carboxylic acid (1.0 g, 3.7 mmol, yield 85%) as a white solid. MS (ESI): m/z 270.6 [M+1]+.

Aufarbeitung

  1. customWhen the starting material was consumed
  2. filtrationThe solids were collected by filtration
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8e8277f02d4d48ef8eb0698a9da3d059
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139534B2

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