Ethanol → HCID 12778919, compound

HRID 1163862Notes

Reaction equation

HRID 1163862 reaction equation
[NH2:1][C:2]1[NH:3][CH2:4][CH2:5][CH:6]=1.[CH2:7]([C:9](CC)([O:11][CH:12]=[C:13]([C:17]([O-:19])=O)[C:14]([O-])=O)C)C.C([OH:24])C>>[O:19]=[C:17]1[C:13]([C:12]([O:11][CH2:9][CH3:7])=[O:24])=[CH:14][N:3]2[CH2:4][CH2:5][CH2:6][C:2]2=[N:1]1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 18368243HCID 18368243, compoundHCID 131712922HCID 131712922, compound

Product 1

HCID 12778919HCID 12778919, compoundYield 17%

Conditions

Temperature
-10 °C

Procedure

50.5 g of 2-amino-pyrroline are dissolved in 600 ml. of ethanol and the solution is cooled to -10° C., and added dropwise under stirring at -10° C. to a solution of 127.8 g. of diethyl-ethoxy-methylene-malonate in 200 ml. of ethanol within 3 hours. The reaction mixture is then stirred for a further 1 hour at 0° C. and allowed to stand for 24 hours. The ethanol is distilled off at reduced pressure and the residual yellow oil, containing a mixture of ethyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-3-carboxylate and ethyl 2-oxo-2,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidino-3-carboxylate at a ratio of 4:1 is dissolved under boiling in 400 ml. benzene. The benzene solution is allowed to crystallize under cooling. The precipitated crystals are filtered. 22 g. (17%) of ethyl 2-oxo-2,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-3-carboxylate are obtained, melting at 193° C. after recrystallization from ethanol.

Workup

  1. additionadded dropwise
  2. stirringThe reaction mixture is then stirred for a further 1 hour at 0° C.
  3. distillationThe ethanol is distilled off at reduced pressure
  4. additionthe residual yellow oil, containing
  5. additiona mixture of ethyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-3-carboxylate and ethyl 2-oxo-2,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidino-3-carboxylate at a ratio of 4:1
  6. dissolutionis dissolved
  7. customto crystallize
  8. temperatureunder cooling
  9. filtrationThe precipitated crystals are filtered

Sources & evidence

ORD record
ord-b0914cbf7efc49389e07a97dc339c174
Source dataset
uspto-grants-1983_01
Patent number
US04367229

Reaction notes

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