Ethyl Acetate → Methyl 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate

HRID 2219042Notes

Reaction equation

HRID 2219042 reaction equation
Cl.[NH:2]=[C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][NH:4]1.[CH2:9]([O:16][CH:17]([C:22](=O)[C:23]([O:25][CH3:26])=[O:24])[C:18](OC)=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1CCN2C(=NCCC2)CC1.CCOC(C)=O>CO>[CH2:9]([O:16][C:17]1[C:18](=[O:19])[N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:3]2=[N:2][C:22]=1[C:23]([O:25][CH3:26])=[O:24])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59771073Dimethyl 2-(benzyloxy)-3-oxosuccinateHCID 178479080HCID 178479080, compound

Product 1

HCID 59771042Methyl 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Commercially available 2-iminopiperidine hydrochloride (1.5 eq) was added at room temperature to a solution of oxosuccinate prepared in Step 1b (1 eq) in MeOH. After dropwise addition of neat DBU (4.5 eq), the reaction mixture was stirred for 2 days. Evaporation of the solvent gave a residue that was taken into EtOAc and washed with 1N HCl and brine; the organic layer was dried on Na2SO4 and the solvent removed. The crude was used without further purification.

Workup

  1. customEvaporation of the solvent
  2. customgave a residue that
  3. washwashed with 1N HCl and brine
  4. customthe organic layer was dried on Na2SO4
  5. customthe solvent removed
  6. customThe crude was used without further purification

Sources & evidence

ORD record
ord-9d22f86b9a6c4d4baf3b27f9553a02c2
Source dataset
uspto-grants-2008_08
Patent number
US07414045B2

Reaction notes

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