Ethyl bromoacetate → (2-Amino-6-iodopurin-9-yl)-acetic acid ethyl ester

HRID 349617

Reaktionsgleichung

Reaktionsgleichung von HRID 349617
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([I:11])[N:3]=1.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([NH2:1])=[N:3][C:4]=2[I:11])[CH3:18]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 61015752-Amino-6-iodopurine

Produkt 1

HCID 85849531(2-Amino-6-iodopurin-9-yl)-acetic acid ethyl esterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-6-iodo-purine (78.3 g, 0.3 mol) in DMF (1960 mL) was added ethyl bromoacetate (55.1 g, 0.33 mol) and potassium carbonate (82.9 g, 0.6 mol). The resulting reaction mixture was stirred for 12 h at room temperature. The reaction mixture was concentrated to small volume (about 150 mL) in vacuo and the residue was dissolved in water. The solid was filtered off, washed with water and ethyl ether, and dried in vacuo to give the titled compound (98.4 g, 95%). 1H-NMR (500 MHz; DMSO-d6) δ 8.06 (s, 1H), 6.90 (br.s, 2H), 4.94 (s, 2H), 4.17 (q, 2H), 1.22 (t, 3H).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated to small volume (about 150 mL) in vacuo
  3. dissolutionthe residue was dissolved in water
  4. filtrationThe solid was filtered off
  5. washwashed with water and ethyl ether
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eaa9194d6ff0453c91e790226098617c
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179896B2

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