Pteridine → 6,7-Bis(3-hydroxyphenyl)-pteridine-2,4-diamine methanesulfonate salt

HRID 1272465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1272465
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[C:15](=[N:16][C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=2)[N:14]=[C:13]([NH2:25])[N:12]=[C:11]3[NH2:26])[CH:5]=[CH:6][CH:7]=1.[CH3:27][S:28]([OH:31])(=[O:30])=[O:29].N1C2C(=NC=CN=2)C=NC=1.C(OCC)C>CO>[CH3:27][S:28]([OH:31])(=[O:30])=[O:29].[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[C:15](=[N:16][C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=2)[N:14]=[C:13]([NH2:25])[N:12]=[C:11]3[NH2:26])[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 1043PteridineHCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 10427712TG-100115

Produkt 1

HCID 865941376,7-Bis(3-hydroxyphenyl)-pteridine-2,4-diamine methanesulfonate saltAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

2.66 g (7.68 mmol) of 6,7-bis(3-hydroxyphenyl)-pteridine-2,4-diamine was added to a solution of 1.55 g (16.13 mmol) of methanesulfonic acid in 20 mL of MeOH with stirring. Pteridine immediately dissolved to give a dark-greenish solution. The reaction mixture was stirred for 30 min and then added dropwise to 400 mL of diethyl ether with vigorous stirring. The formed yellow precipitate was collected, washed repeatedly with ether and dried in vacuo to give 3.36 g (99.1% yield) of the product as a light-yellow powder. 95.5% purity by LC/MS (230 DAD). Mass-spec [ES+]=347. 1H NMR (MeOH-d4) 2.71 (3H, s), 6.80–6.85 (2H, m), 6.90–6.92 (2H, m), 6.95 (1H, m), 7.00 (1H, m), 7.12–7.16 (2H, m).

Aufarbeitung

  1. customto give a dark-greenish solution
  2. stirringThe reaction mixture was stirred for 30 min
  3. customThe formed yellow precipitate was collected
  4. washwashed repeatedly with ether
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f57eab96093c4b799abdab9fa327cc7b
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208493B2

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