Diethyl (ethoxymethylene)malonate → HCID 10449422, compound

HRID 542895Notes

Reaction equation

HRID 542895 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[C:9]([CH3:11])=[N:10][C:5]2=[CH:4][CH:3]=1.C(O[CH:16]=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])C>C1(C)C=CC=CC=1>[CH2:26]([O:25][C:23]([C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][NH:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[C:9]([CH3:11])=[N:10][C:5]2=[CH:4][CH:3]=1)=[O:24])[CH3:27]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 102411102,3-Dimethyl-3H-imidazo[4,5-b]pyridin-5-amine

Product 1

HCID 10449422HCID 10449422, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-amino-2,3-dimethyl-3H-imidazo-[4,5-b]pyridine (4.86 g) and 2-ethoxy-1,1-bis-(ethoxycarbonyl)ethene (7.13 g) in toluene (200 ml) was stirred and heated at reflux for 2 hours and then it was evaporated to dryness. The residue was extracted 3 times with boiling petroleum ether (b.p. 80°-100° C.), the extracts were filtered while hot and the filtrate was then cooled to 0° C. The resulting yellow solid was filtered off, to give 1,1-bis(ethoxycarbonyl)-2-(2,3-dimethyl-3H-imidazo-[4,5-b]pyrid-5-ylamino)ethene (8.4 g) in the form of a yellow sold, m.p. 128°-130° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customit was evaporated to dryness
  4. extractionThe residue was extracted 3 times with boiling petroleum ether (b.p. 80°-100° C.)
  5. filtrationthe extracts were filtered while hot and the filtrate
  6. filtrationThe resulting yellow solid was filtered off

Sources & evidence

ORD record
ord-bc255519a2d0483aada5f6a5981b3da3
Source dataset
uspto-grants-1987_04
Patent number
US04659727

Reaction notes

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