Diethyl Oxalate → Ethyl 6-(benzyloxy)-1-(2-methoxyethyl)-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate

HRID 1726905Notes

Reaction equation

HRID 1726905 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2](OCC)=O.[CH2:11]([O:18][CH2:19][C:20]([O:22]CC)=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Br.[CH3:28][O:29][CH2:30][CH2:31][N:32]1[CH2:36][CH2:35][N:34]=[C:33]1[NH2:37]>>[CH2:11]([O:18][C:19]1[C:20](=[O:22])[N:34]2[CH2:35][CH2:36][N:32]([CH2:31][CH2:30][O:29][CH3:28])[C:33]2=[N:37][C:2]=1[C:1]([O:8][CH2:9][CH3:10])=[O:7])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 290299Ethyl 2-(benzyloxy)acetateHCID 690265891-(2-Methoxyethyl)-4,5-dihydro-1H-imidazol-2-amine hydrobromide

Product 1

HCID 57565037Ethyl 6-(benzyloxy)-1-(2-methoxyethyl)-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylateYield 12.4%

Procedure

Reaction of the adduct of diethyl oxalate (16.95 g, 0.116 mol), ethyl benzyloxyacetate (22.53 g, 0.116 mol) and sodium hydride (5.10 g of a 60% dispersion in mineral oil, 0.127 mol) with 1-(2-methoxyethyl)-4,5-dihydro-1H-imidazol-2-amine hydrobromide (26.0 g, 0.116 mol) as described for intermediate 1 gave 5.37 g (12% yield) of the title ester as a clear oil. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.31 (3H, t, J=7.1 Hz, CH3), 3.38 (3H, s, OCH3), 3.61 (4H, s, 2×CH2), 3.84 (2H, t, J=8.9 Hz, CH2), 4.14 (2H, t, J=8.9 Hz, CH2), 4.32 (2H, q, J=7.1 Hz, OCH2), 5.09 (2H, s, OCH2), 7.3-7.38 (3H, m, aromatics), 7.49 (2H, m, aromatics). MS (ESI+) m/e 374 [M+H+].

Sources & evidence

ORD record
ord-7355e9d1ba66481b90fd6a4a2f6dd775
Source dataset
uspto-grants-2009_02
Patent number
US07494984B2

Reaction notes

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