Methyl acetoacetate → HCID 14098292, compound

HRID 648455Notes

Reaction equation

HRID 648455 reaction equation
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[N:11][C:6]2=[N:5][CH:4]=1)=O.[NH2:12]/[C:13](/[CH3:19])=[CH:14]\[C:15]([O:17][CH3:18])=[O:16].[C:20]([O:26][CH3:27])(=[O:25])[CH2:21][C:22]([CH3:24])=O>C(O)(C)C.CCOCC>[CH3:19][C:13]1[NH:12][C:22]([CH3:24])=[C:21]([C:20]([O:26][CH3:27])=[O:25])[CH:1]([C:3]2[N:7]3[CH:8]=[CH:9][CH:10]=[N:11][C:6]3=[N:5][CH:4]=2)[C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 3

HCID 7757Methyl acetoacetateHCID 404535imidazo[1,2-a]pyrimidine-3-carbaldehydeHCID 643918Methyl 3-aminocrotonate

Product 1

HCID 14098292HCID 14098292, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

To 0.5 g (3.4 mmol) (2) in 10 ml isopropanol was added 0.39 g (3.4 mmol) methyl 3-aminocrotonate and 0.39 g (3.4 mmol) methyl acetoacetate and the resulting solution refluxed overnight. The cooled reaction mixture was then diluted with 15 ml ether and stirred for 1 hour. The tan solid was filtered off and recrystallized from ethyl acetate to give pure (3), m.p. 202°-205° (dec).

Workup

  1. temperaturethe resulting solution refluxed overnight
  2. customThe cooled reaction mixture
  3. filtrationThe tan solid was filtered off
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-24719ea08c054aa69393062f22cb3349
Source dataset
uspto-grants-1988_04
Patent number
US04735956

Reaction notes

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