1,2-Dimethylhydrazine dihydrochloride → HCID 18442536, compound

HRID 458688

Reaction equation

[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

Participants

Conditions

Temperature: 22 °C

Procedure

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.

Workup

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)

Sources & evidence

ORD record: ord-c4ad857185174b728b2b069bd279f61c
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192948B2

Linked notes

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