Bicarbonate Ion → 6-{[2-(3,4-Dimethoxy-phenyl)ethylamino]-methyl}-2,4-pteridinediamine

HRID 1272486

Reaktionsgleichung

Reaktionsgleichung von HRID 1272486
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].Cl.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][NH2:29])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26].C(=O)(O)[O-]>CN(C)C(=O)C>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][NH:29][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:22]=[CH:23][C:24]=1[O:25][CH3:26]

Komponenten

5

Edukt 3

HCID 769Bicarbonate IonHCID 71555Homoveratrylamine hydrochlorideHCID 125032426-(Bromomethyl)-2-imino-2,3-dihydropteridin-4-amine--hydrogen bromide (1/1)

Produkt 1

HCID 184557266-{[2-(3,4-Dimethoxy-phenyl)ethylamino]-methyl}-2,4-pteridinediamineAusbeute 19,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 6-bromomethyl-2,4-pteridinediamine hydrobromide (55 mg, 0.1638 mmol) in anhydrous N,N dimethylacetamide was added 2-(3,4-dimethoxyphenyl) ethylamine hydrochloride (55 ul, 0.32 mmol). The reaction mixture was stirred at 50° C. overnight. The crude product was poured into saturated bicarbonate solution. The resulted precipitate was collected and purified by preparative HPLC. 3.8 mg product was obtained. Yield: 19.6%; 1H NMR (500 MHz, DMSO-d6): δ 2.75943–2.79062 (t, J=7.37 Hz, 2H), 2.92110–2.95356 (t, J=7.365 Hz, 2H), 3.72197(s, 3H), 3.75135(s, 3H), 4.54559(s, 2H), 6.74441–6.77765 (dd, J1=8.26 Hz, J2=1.955 Hz, 1H), 6.84994 (s, 1H), 6.88406–6.90401 (dd, J1=8.195 Hz, J2=1.735 Hz, 1H); 8.87126(s, 1H); ESI-MS: m/z 356 (M++1)

Aufarbeitung

  1. customThe resulted precipitate was collected
  2. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9e5bf78a5c8345fd9d57165747bd8406
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208493B2

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