Dimethylformamide dimethyl acetal → HCID 178448720, compound

HRID 377610Notes

Reaction equation

HRID 377610 reaction equation
[NH:1]([C:3]1[N:8]([CH2:9][C:10]([CH3:12])=[CH2:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5](=[O:15])[CH:4]=1)[NH2:2].[CH3:16]OC(OC)N(C)C>>[CH3:14][N:6]1[C:5](=[O:15])[C:4]2=[CH:16][NH:2][N:1]=[C:3]2[N:8]([CH2:9][C:10]([CH3:12])=[CH2:11])[C:7]1=[O:13]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 19356092HCID 19356092, compound

Product 1

HCID 178448720HCID 178448720, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 6-hydrazino-3-methyl-1-(2-methyl-2-propenyl)pyrimidine-2,4[1H,3H]-dione (0.575 g) and dimethylformamide dimethylacetal (0.73 ml) was heated at 90° C. for 20 minutes. The mixture was allowed to cool and was directly purified by column chromatography over silica eluting with ethyl acetate: hexane (2:1) and then recrystallisation from ethyl acetate/hexane to give the subtitle compound (0.063 g). Melting point: 232-233° C. MS (EI) 220 (M+) 1H NMR (CDCl3 /DMSO-d6) δ 1.80 (3H, s); 3.39 (3H, s); 4.60 (2H, s); 4.75 (1H, s), 4.89 (1H, s); 8.04 (1H, s); 13.04 (1H, s, br).

Workup

  1. temperatureto cool
  2. customwas directly purified by column chromatography over silica eluting with ethyl acetate: hexane (2:1)
  3. customrecrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-dc01b1c316f34c8fb8520f323f3d3d25
Source dataset
uspto-grants-2000_02
Patent number
US06028074

Reaction notes

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