Methanol → 4-[(3-Chloro-4-methoxybenzyl)amino]-2-[(2S)-2-(hydroxymethyl)-pyrrolidin-1-yl]pyrimidine-5-carboxylic acid

HRID 2200908

Reaktionsgleichung

Reaktionsgleichung von HRID 2200908
CO.[Cl:3][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:7][NH:8][C:9]1[C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][N:12]=[C:11]([N:20]2[CH2:24][CH2:23][CH2:22][C@H:21]2[CH2:25][OH:26])[N:10]=1.O.[Na]>O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:7][NH:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=[C:11]([N:20]2[CH2:24][CH2:23][CH2:22][C@H:21]2[CH2:25][OH:26])[N:10]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 52348789Ethyl 4-((3-chloro-4-methoxy-phenyl)methylamino)-2-((2S)-2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylateHCID 71353970Sodium monohydrate

Produkt 1

HCID 671193354-[(3-Chloro-4-methoxybenzyl)amino]-2-[(2S)-2-(hydroxymethyl)-pyrrolidin-1-yl]pyrimidine-5-carboxylic acidAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Methanol (50 mL) was added in ethyl (s)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidine carboxylate (8.75 g, 20.8 mmol). In water (20 mL) was dissolved sodium hydrate (1.66 g, 41.6 mmol), then the aqueous solution was added to the reaction solution. The reaction was conducted in an oil bath of 50 to 60° C. overnight. The reaction was monitored by LC-MS. The organic solvent was removed by rotary evaporation. The residual aqueous phase was adjusted to a pH of 3 to 4. Then solid was precipitated. The precipitation was filtrated and dried to give a solid (3.9 g, 48.1% yield).

Aufarbeitung

  1. additionthe aqueous solution was added to the reaction solution
  2. customThe organic solvent was removed by rotary evaporation
  3. customThen solid was precipitated
  4. customThe precipitation
  5. filtrationwas filtrated
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-caed84a4441748fb83a08326067543fe
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359371B2

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