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

HRID 1013635Notes

Reaction equation

HRID 1013635 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-e2a3a80758684428b7001ed5c43d99d5
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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