Acetamide, N-methoxy-2-[(4-methoxyphenyl)methoxy]-N-methyl- → 2-[(4-Methoxybenzyl)oxy]-1-[5-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,3-thiazol-2-yl]ethanone

HRID 40907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 40907
[S:1]1[C:5]([C:6]2[C:7]3[CH:14]=[CH:13][N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=3[N:9]=[CH:10][N:11]=2)=[CH:4][N:3]=[CH:2]1.C([Li])CCC.CON(C)[C:31](=[O:43])[CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1>C1COCC1.CCCCCC>[CH3:42][O:41][C:38]1[CH:39]=[CH:40][C:35]([CH2:34][O:33][CH2:32][C:31]([C:2]2[S:1][C:5]([C:6]3[C:7]4[CH:14]=[CH:13][N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=4[N:9]=[CH:10][N:11]=3)=[CH:4][N:3]=2)=[O:43])=[CH:36][CH:37]=1

Komponenten

6

Edukt 3

HCID 11424955Acetamide, N-methoxy-2-[(4-methoxyphenyl)methoxy]-N-methyl-HCID 574776204-(1,3-thiazol-5-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidineHCID 178418339Butyllithium

Produkt 1

HCID 574776382-[(4-Methoxybenzyl)oxy]-1-[5-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,3-thiazol-2-yl]ethanoneAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(1,3-thiazol-5-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine (2.12 g, 6.38 mmol) in THF (70 mL) at −78° C. was added 2.5 M n-butyllithium in hexane (3.06 mL) slowly dropwise. After stirring for 30 minutes, N-methoxy-2-[(4-methoxybenzyl)oxy]-N-methylacetamide (2.29 g, 9.56 mmol) was added. The reaction was continued for 30 minutes following the addition, at −78° C., then the cooling bath was removed and the reaction was quenched with saturated ammonium chloride and extracted with ether. The extracts were dried with sodium sulfate and concentrated in vacuo. The crude mixture was purified by flash column chromatography (ethyl acetate/hexanes) to afford desired product (2.16 g, 66%).

Aufarbeitung

  1. waitThe reaction was continued for 30 minutes
  2. additionthe addition
  3. customat −78° C., then the cooling bath was removed
  4. customthe reaction was quenched with saturated ammonium chloride
  5. extractionextracted with ether
  6. dry with materialThe extracts were dried with sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude mixture was purified by flash column chromatography (ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3db5fc77452447ba9d8ab018810df480
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530485B2

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