Sodium hydride → 5-(4-phenoxyphenyl)-7-(1,4-dioxaspiro[4.5]decan-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 51507

Reaktionsgleichung

Reaktionsgleichung von HRID 51507
[H-].[Na+].[O:3]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:24]3[C:23]([NH2:25])=[N:22][CH:21]=[N:20][C:19]=3[NH:18][CH:17]=2)=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].S(O[CH:39]1[CH2:48][CH2:47][C:42]2([O:46][CH2:45][CH2:44][O:43]2)[CH2:41][CH2:40]1)(C1C=CC(C)=CC=1)(=O)=O.O1C2(CCC(=O)CC2)OCC1>CN(C)C=O>[O:3]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[C:24]3[C:23]([NH2:25])=[N:22][CH:21]=[N:20][C:19]=3[N:18]([CH:39]3[CH2:48][CH2:47][C:42]4([O:46][CH2:45][CH2:44][O:43]4)[CH2:41][CH2:40]3)[CH:17]=2)=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

7

Edukt 5

HCID 24758Sodium hydrideHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5674891,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)HCID 120422345-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 227362315-(4-phenoxyphenyl)-7-(1,4-dioxaspiro[4.5]decan-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Sodium hydride (0.26 g of a 60% dispersion in mineral oil) was added to a mixture of 5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (1.94 g) in dimethylformamide 950 ml) at ambient temperature with stirring. The mixture was stirred until the evolution of hydrogen ceased and then 8-tosyloxy-1,4-dioxaspiro[4,5]decane (2.0 g, prepared as described in U.S. Pat. No. 4,360,531 from 1,4-dioxaspiro[4,5]decan-8-one, (which was prepared according to J. Med. Chem. 1992, 22460) was added. The mixture was heated at 120° C. for 5 hours under nitrogen, cooled to ambient temperature, quenched with water and extracted with ethyl acetate to give a residue which was purified by flash column chromatography on silica using ethyl acetate followed by ethyl acetate containing increasing amounts of methanol up to 6% to give 5-(4-phenoxyphenyl)-7-(1,4-dioxaspiro[4,5]decan-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, m.p. 193-194° C.

Aufarbeitung

  1. additionwas added
  2. temperaturecooled to ambient temperature
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. customto give a residue which
  6. customwas purified by flash column chromatography on silica
  7. temperatureincreasing amounts of methanol up to 6%

Quellen und Nachweise

ORD-Eintrag
ord-24151eaa461544c7976eeeb6d9b9783c
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713474B2

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