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Potassium Hydroxide → 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionic acid

HRID 51500
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 51500
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]([CH3:30])[C:25]([O:27]CC)=[O:26])[C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[K+]>CO>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]([CH3:30])[C:25]([OH:27])=[O:26])[C:4]=2[N:5]=[CH:6][N:7]=1
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Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 22736339ethyl 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionate

Produkt 1

HCID 227363532-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionate (201 mg), aqueous potassium hydroxide solution (4 ml of 2M solution) and methanol (20 ml) was boiled under reflux for 1 hour. The mixture was concentrated under reduced pressure to around 5 ml and then diluted with water (30 ml). The mixture was hot filtered and filtrate was cooled and then acidified with dilute acetic acid until no further precipitation occurred. The mixture was heated on a hot plate until the gel which had been obtained became a finely divided solid. The solid was collected by filtration to give 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionic acid, m.p. 239.5-241° C.

Aufarbeitung

  1. temperatureunder reflux for 1 hour
  2. concentrationThe mixture was concentrated under reduced pressure to around 5 ml
  3. additiondiluted with water (30 ml)
  4. filtrationThe mixture was hot filtered
  5. temperaturefiltrate was cooled
  6. customacidified with dilute acetic acid until no further precipitation
  7. temperatureThe mixture was heated on a hot plate until the gel which
  8. customhad been obtained
  9. filtrationThe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-3e4ee56c3e2b413d9dc774cc6b0491a5
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06713474B2

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