1,2-Dimethylhydrazine dihydrochloride → HCID 18442536, Verbindung

HRID 458688

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH2:16][C:17]([O:19]C)=O)[C:12](S(C)(=O)=O)=[N:11][C:10]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[CH3:32][NH:33][NH:34][CH3:35].C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[C:12]([N:33]([CH3:32])[N:34]([CH3:35])[C:17](=[O:19])[CH2:16]2)=[N:11][C:10]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 22 °C

Versuchsvorschrift

A mixture of intermediate 3, ethyl 5-benzyloxy-1-(methoxycarbonylmethyl)-2-(methylsulfonyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate, (0.487 g, 1.15 mmol) in N,N-dimethylformamide (25 ml) was treated with 1,2-dimethylhydrazine dihydrochloride (1.56 g, 11.7 mmol) followed by N,N-diisopropylethylamine (4.1 ml, 11.7 mmol) and the resulting mixture stirred at 22° C. for 4 h. The solvent was then removed in vacuo and the residue diluted with ethyl acetate, washed successively with saturated sodium bicarbonate and brine then dried over anhydrous magnesium sulfate. Evaporation of the solvent followed by chromatography on silica gel (elution with a gradient of ethyl acetate 0–50% in toluene) gave 0.294 g (69% yield) of the title ester as a clear syrup.

Aufarbeitung

customThe solvent was then removed in vacuo
additionthe residue diluted with ethyl acetate
washwashed successively with saturated sodium bicarbonate and brine
dry with materialthen dried over anhydrous magnesium sulfate
customEvaporation of the solvent
washelution with a gradient of ethyl acetate 0–50% in toluene)

Quellen und Nachweise

ORD-Eintrag: ord-c4ad857185174b728b2b069bd279f61c
Quelldatensatz: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07192948B2

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