Bicarbonate Ion → 6-[{(Pyridin-2-ylmethyl)-amino]-methyl}-2,4-pteridinediamine

HRID 1272481

Reaktionsgleichung

Reaktionsgleichung von HRID 1272481
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].[NH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.C(=O)(O)[O-]>CN(C)C(=O)C>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][NH:16][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]

Komponenten

5

Edukt 3

HCID 769Bicarbonate IonHCID 195092-PyridinemethanamineHCID 125032426-(Bromomethyl)-2-imino-2,3-dihydropteridin-4-amine--hydrogen bromide (1/1)

Produkt 1

HCID 103790346-[{(Pyridin-2-ylmethyl)-amino]-methyl}-2,4-pteridinediamineAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 6-bromomethyl-2,4-pteridinediamine hydrobromide (51 mg, 0.2 mmol) in anhydrous N,N dimethylacetamide was added 2-(aminomethyl) pyridine (22.48 ul, 0.22 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. 32.3 mg product was obtained. Yield: 57%; 1H NMR (500 MHz, DMSO-d6): δ 3.93801 (s, 2H), 4.05772(s, 2H), 7.5758–7.6003 (m, 1H), 7.97993–8.00181 (m, 1H), 8.49332–8.50942 (d, J=8.05 Hz, 1H), 8.62592–8.64301 (d, J=8.545 Hz, 1H), 8.9938(s, 1H); ESI-MS: 283 (M++1)

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-48e7121c13d74907b1f799b5b590e9b3
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208493B2

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