Hydrochloric Acid → 6-Benzyloxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylic acid

HRID 458684Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][C:17](=[O:20])[N:18]([CH3:19])[C:12]2=[N:11][C:10]=1[C:21]([O:23]CC)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl.C(OCC)(=O)C>C(O)C.O1CCCC1>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][C:17](=[O:20])[N:18]([CH3:19])[C:12]2=[N:11][C:10]=1[C:21]([OH:23])=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of intermediate 12, ethyl 6-benzyloxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate, (0.084 g, 0.24 mmol) in a mixture of ethanol (5 ml) and tetrahydrofuran (5 ml) was treated with 1.0 ml of a 1 M aqueous sodium hydroxide and the resulting mixture was stirred at 25° C. for 30 min. The reaction mixture was then acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and concentrated to give 0.073 g (95% yield) of the title acid as white crystals; mp 194° C. (ethyl acetate). 1HNMR 400 MHz (DMSO-d6) δ (ppm): 3.07 (3H, s, NCH3), 4.54 (2H, s, CH2), 5.04 (2H, s, CH2), 7.3–7.5 (5H, m, aromatics), 13.8 (1H, s, OH). MS (ESI+) m/z 316 [M+H+].

Workup

extractionextracted with ethyl acetate
washThe organic phase was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customto give 0.073 g (95% yield) of the title acid as white crystals

Sources & evidence

ORD record: ord-b6f688afe8ec498083b9329dc6b54839
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192948B2

Reaction notes

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