Dopamine → 6-{[2-(3,4-Dihydroxy-phenyl)ethylamino]-methyl}-2,4-pteridinediamine

HRID 1272487

Reaktionsgleichung

Reaktionsgleichung von HRID 1272487
Br.Br[CH2:3][C:4]1[N:5]=[C:6]2[C:11](=[N:12][CH:13]=1)[N:10]=[C:9]([NH2:14])[N:8]=[C:7]2[NH2:15].[OH:16][C:17]1[CH:18]=[C:19]([CH2:24][CH2:25][NH2:26])[CH:20]=[CH:21][C:22]=1[OH:23].C(N(C(C)C)C(C)C)C.C(=O)(O)[O-]>CN(C)C(=O)C>[OH:16][C:17]1[CH:18]=[C:19]([CH2:24][CH2:25][NH:26][CH2:3][C:4]2[N:5]=[C:6]3[C:11](=[N:12][CH:13]=2)[N:10]=[C:9]([NH2:14])[N:8]=[C:7]3[NH2:15])[CH:20]=[CH:21][C:22]=1[OH:23]

Komponenten

6

Edukt 4

HCID 681DopamineHCID 769Bicarbonate IonHCID 81531DiisopropylethylamineHCID 125032426-(Bromomethyl)-2-imino-2,3-dihydropteridin-4-amine--hydrogen bromide (1/1)

Produkt 1

HCID 184557256-{[2-(3,4-Dihydroxy-phenyl)ethylamino]-methyl}-2,4-pteridinediamineAusbeute 22,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 6-bromomethyl-2,4-pteridinediamine hydrobromide (67.3 mg, 0.2003 mmol) in anhydrous N,N dimethylacetamide was added 2-(3,4-dihydroxyphenyl) ethylamine (43.6 mg, 0.23 mmol). Under positive pressure of Argon, iPr2EtN (32.63 ul) was added. The reaction mixture was stirred at 50° C. for 4 hrs and then at Room temperature overnight. The crude product was poured into saturated bicarbonate solution. The resulted precipitate was collected and purified by preparative HPLC. 14.8 mg product was obtained. Yield: 22.6%; 1H NMR (500 MHz, DMSO-d6): δ 2.69242 (b, 4H), 4.03353 (s, 2H), 6.37542–6.39065 (d, J=7.615 Hz, 1H), 6.4851(s, 1H), 6.56632–6.58226 (d, J=7.97 Hz, 1H), 8.80972 (s, 1H); ESI-MS: m/z 328 (M++1)

Aufarbeitung

  1. customat Room temperature
  2. customovernight
  3. customThe resulted precipitate was collected
  4. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-09e79be0cd044caa97d569d8e6d6e144
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208493B2

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