Triethylamine → 3-{2-[(Quinolin-4-ylmethyl)amino]ethyl}-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one

HRID 912721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 912721
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][N:11]1[C:19]2[N:18]=[CH:17][NH:16][C:15]=2[C:14](=[O:20])[NH:13][C:12]1=[S:21].C(N(CC)CC)C.[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH:39]=O)=[CH:31][CH:30]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH2:39][NH:8][CH2:9][CH2:10][N:11]2[C:19]3[N:18]=[CH:17][NH:16][C:15]=3[C:14](=[O:20])[NH:13][C:12]2=[S:21])=[CH:31][CH:30]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 780724-QuinolinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 866311443-(2-Aminoethyl)-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one trifluoroacetate

Produkt 1

HCID 248556323-{2-[(Quinolin-4-ylmethyl)amino]ethyl}-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-oneAusbeute 29,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

3-(2-Aminoethyl)-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one trifluoroacetate (98 mg, 0.3 mmol, obtained from Example 26(b)) and triethylamine (0.043 mL, 0.31 mmol) was stirred in dry methanol for 15 min. 4-Quinoline carboxaldehyde (47 mg, 0.3 mmol) and acetic acid (3 drops) were added and the mixture was stirred o.n. Sodium cyanoborohydride (28 mg, 0.45 mmol) was added and the mixture was stirred for 5 h. The mixture was then concentrated and purified by preparative HPLC, giving 31 mg (29% yield) of the title compound

Aufarbeitung

  1. stirringthe mixture was stirred for 5 h
  2. concentrationThe mixture was then concentrated
  3. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-333418bff52140bbb290a4d8ae64fd74
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026244B2

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