Trimethyl orthoformate → 1,3-Dioxane-4,6-dione, 5-[[(6-methoxy-3-pyridinyl)amino]methylene]-2,2-dimethyl-

HRID 503510Notes

Reaction equation

HRID 503510 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH:11](OC)(OC)OC.[CH3:18][O:19][C:20]1[N:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1>CCCCCC>[CH3:18][O:19][C:20]1[N:25]=[CH:24][C:23]([NH:26][CH:11]=[C:6]2[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:5])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 811216-Methoxy-3-pyridinylamine

Product 1

HCID 42557991,3-Dioxane-4,6-dione, 5-[[(6-methoxy-3-pyridinyl)amino]methylene]-2,2-dimethyl-

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of Meldrum's acid (34.8 g, 0.242 mol) and trimethyl orthoformate (285 mL, 2.05 mol) was heated to 105° C. for 2 h. To the solution 6-methoxypyridin-3-amine (30 g, 0.242 mol) was added and continued the stirring overnight at the same temperature. The mixture was allowed to cool to RT and diluted with hexane. The solid precipitated was filtered and washed with hexane to afford 5-((6-methoxypyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione as a pale yellow solid.

Workup

  1. customthe stirring overnight
  2. temperatureto cool to RT
  3. customThe solid precipitated
  4. filtrationwas filtered
  5. washwashed with hexane

Sources & evidence

ORD record
ord-2a6dbf4eacd246a9b7f1de52d64074a7
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

Loading…