Sodium hydride → ethyl 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionate

HRID 51497

Reaktionsgleichung

Reaktionsgleichung von HRID 51497
[H-].[Na+].[NH2:3][C:4]1[C:5]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)=[CH:11][NH:10][C:6]=2[N:7]=[CH:8][N:9]=1.Br[CH:27]([CH3:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29]>CN(C)C=O>[NH2:3][C:4]1[C:5]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:17][CH:18]=3)=[CH:11][N:10]([CH:27]([CH3:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:6]=2[N:7]=[CH:8][N:9]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionateHCID 120422345-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Sodium hydride (120 mg, of a 60% dispersion in mineral oil) was added to a mixture of 4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine (906 mg) in dry dimethyformamide (30 ml) and the mixture was stirred under nitrogen for 30 minutes at ambient temperature. A solution of ethyl 2-bromopropionate (543 mg) in dry DMF (10 ml) was added dropwise via a syringe over 10 minutes. The mixture was stirred at ambient temperature for 2 hours and then left for 18 hours. The mixture was evaporated under vacuum and the residue was washed with water to give a solid which was triturated with ether and filtered to give ethyl 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionate, m.p. 139-140° C.

Aufarbeitung

  1. stirringThe mixture was stirred at ambient temperature for 2 hours
  2. waitleft for 18 hours
  3. customThe mixture was evaporated under vacuum
  4. washthe residue was washed with water
  5. customto give a solid which
  6. customwas triturated with ether
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-710ab7225e9043369c56d7d03f1dd4b3
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713474B2

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