N,O-bis(trimethylsilyl)acetamide → 2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

HRID 2239806

Reaktionsgleichung

Reaktionsgleichung von HRID 2239806
[NH2:1][C:2]1[N:3]=[C:4]([NH:11][NH:12][C:13]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)=O)[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.CC1(C)[SiH2][SiH]=NC(C)(C)C1(C)C>>[O:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[C:13]1[N:3]=[C:4]2[N:11]([C:2]([NH2:1])=[N:7][C:6]3[NH:8][CH:9]=[CH:10][C:5]=32)[N:12]=1

Komponenten

4

Edukt 3

HCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 68413686N'-(2-amino-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazideHCID 1317189914,4,5,5,6,6-hexamethyl-3H-azadisiline

Produkt 1

HCID 1363878362-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of the title A compound, N′-(2-amino-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide (0.4 g, 1.55 mmol), N,O-bis(trimethylsilyl)acetamide (1.89 g, 9.3 mmol) and 2 mL of hexamethyldisilazine is heated at 120° C. overnight. After removing volatiles under vacuum, the residue is washed with 5 mL of water and the collected solid is purified by flash chromatography using EtOAc/MeOH (95/5) as eluent to give 2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine: LC/MS (M+1=241.0). 1H NMR (DMSO-d6, 400 MHz) δ 6.57 (m, 1H), 6.70 (m, 1H), 7.01 (m, 1H), 7.18 (m, 1H), 7.36 (br s, 2H, NH2), 7.89 (s, 1H), 11.6 (br s, NH-pyrrole).

Aufarbeitung

  1. customAfter removing volatiles under vacuum
  2. washthe residue is washed with 5 mL of water
  3. customthe collected solid is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4f7cf0b6854b474fafce742352c92148
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723343B2

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