Sodium hydride → 5-Cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazine

HRID 1357005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1357005
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].[H-].[Na+].[CH:12]1([O:17][C:18]2[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]3[C:19]=2[CH:20]=[N:21][NH:22][CH:23]3Cl)[CH2:16][CH2:15][CH2:14][CH2:13]1>CN(C)C=O>[CH:12]1([O:17][C:18]2[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]3[C:19]=2[CH:20]=[N:21][N:22]=[C:23]3[CH2:8][C:7]2[C:6]([Cl:9])=[CH:5][N:4]=[CH:3][C:2]=2[Cl:1])[CH2:13][CH2:14][CH2:15][CH2:16]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 109538273,5-Dichloro-4-methylpyridineHCID 185048005-cyclopentyloxy-1-chloro-6-methoxy-2H-phthalazine

Produkt 1

HCID 98659165-Cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazineAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3,5-dichloro-4-methyl-pyridine (13.86 g, 85.56 mmoles) in dry dimethylformamide (100 ml) was added, under nitrogen and stirring, with 55% NaH (3.73 g, 85.56 mmoles). The mixture was stirred for 1 hour then added with a solution of 5-cyclopentyloxy-1-chloro-6-methoxy-2H-phthalazine (7.95 g, 28.52 mmoles), obtained as described in example 7, in dry dimethylfomamide (70 ml). The mixture was left to stand for one night, quenched with water, diluted with water and extracted methyl aceate. The extract was washed with water and anhydrified over Na2SO4, then evaporated to dryness. The residue was flash chromatographed (eluent:petrolatum/ethyl acetate 1:1) to give 6.58 g of the title product (yield: 57%).

Aufarbeitung

  1. customobtained
  2. waitThe mixture was left
  3. waitto stand for one night
  4. customquenched with water
  5. additiondiluted with water
  6. extractionextracted methyl aceate
  7. washThe extract was washed with water
  8. customevaporated to dryness
  9. customchromatographed (eluent:petrolatum/ethyl acetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-67c84279d39146c5a9058e0f50976f22
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06589951B1

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