Hydrochloric Acid → 3-(Benzyloxy)-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acid

HRID 348102Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of intermediate 6, ethyl 3-(benzyloxy)-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate (0.300 g, 0.91 mmol) in ethanol (10 ml) was treated with 3 ml (3.0 mmol) of 1 N sodium hydroxide and stirred at 25° C. for 30 min. The solution was then acidified with 1 N hydrochloric acid, extracted with ethyl acetate, washed with brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent gave 0.264 g (96% yield) of the title acid as white crystals; mp 171° C. (ethyl acetate). 1HNMR 400 MHz (CDCl3) δ (ppm): 4.03 (2H, t, J=5.3 Hz, CH2), 4.12 (2H, t, J=5.3 Hz, CH2), 4.73 (2H, s, OCH2), 5.53 (2H, s, OCH2), 7.35–7.42 (3H, m, aromatics), 7.53 (2H, m, aromatics). Anal. Calcd for C15H14N2O5: C, 59.60; H, 4.67; N, 9.27. Found: C, 59.35; H, 4.69; N, 9.10.

Workup

extractionextracted with ethyl acetate
washwashed with brine
dry with materialdried over anhydrous magnesium sulfate
customEvaporation of the solvent
customgave 0.264 g (96% yield) of the title acid as white crystals

Sources & evidence

ORD record: ord-1a7a51618a09433cb71294ddac4596bf
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176196B2

Reaction notes

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