Bicarbonate Ion → 6-{[(Naphthalen-1-yl-methyl)-amino]-methyl}-2,4-pteridinediamine

HRID 1272482

Reaktionsgleichung

Reaktionsgleichung von HRID 1272482
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[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C(=O)(O)[O-]>CN(C)C(=O)C>[C:18]1([CH2:17][NH:16][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])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 769Bicarbonate IonHCID 83551-NaphthalenemethanamineHCID 125032426-(Bromomethyl)-2-imino-2,3-dihydropteridin-4-amine--hydrogen bromide (1/1)

Produkt 1

HCID 184557496-{[(Naphthalen-1-yl-methyl)-amino]-methyl}-2,4-pteridinediamineAusbeute 15 %

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 1-aminomethyl-naphthalene (31.67 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. 9 mg product was obtained. Yield: 15%; 1H NMR(500 MHz, DMSO-d6): δ 4.6479(s, 2H ), 4.7893(s, 2H), 7.575–7.6244(m, 3H), 7.74232–7.7570(d, J=6.91 Hz, 1H), 7.9935–8.0276(dd, J1=8.06 Hz, J2 =8.995 Hz, 2H), 8.1670–8.1831(d, J=8.04 Hz, 1H), 8.8430(s, 1H); ESI-MS: m/z 332 (M++1)

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-d75a0c5d00004cd6bb08de995d0f6bfe
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208493B2

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