Bicarbonate Ion → 6-(Benzylamino-methyl)-2,4-pteridinediamine

HRID 1272483

Reaktionsgleichung

Reaktionsgleichung von HRID 1272483
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].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)(O)[O-]>CN(C)C(=O)C>[CH2:16]([NH:23][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])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 769Bicarbonate IonHCID 7504BenzylamineHCID 125032426-(Bromomethyl)-2-imino-2,3-dihydropteridin-4-amine--hydrogen bromide (1/1)

Produkt 1

HCID 184557476-(Benzylamino-methyl)-2,4-pteridinediamineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 6-bromomethyl-2,4-pteridinediamine hydrobromide (35.7 mg, 0.106 mmol) in anhydrous N,N dimethylacetamide was added benzylamine (28.6 ul, 0.212 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. 17.7 mg product was obtained. Yield: 62%; 1H NMR (500 MHz, DMSO-d6): δ 4.30499(s, 2H), 4.51599(s, 2H), 7.42787–7.47298(m, 3H), 7.50007–7.51927 (m, 2H), 8.87751(s, 1H); ESI-MS: m/z 282 (M++1)

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9c0e5e93276546f39777a4f3fceafa60
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208493B2

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