Ethyl 3-(benzyloxy)-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate → Ethyl 3-hydroxy-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate

HRID 348103Notes

Reaction equation

HRID 348103 reaction equation
C([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][CH2:23][CH3:24])=[O:21])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[OH: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][CH2:23][CH3:24])=[O:21]

Participants

6

Reactant 2

HCID 21069950Ethyl 3-(benzyloxy)-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 54708344Ethyl 3-hydroxy-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylateYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of intermediate 6, ethyl 3-benzyloxy-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate, (0.236 g, 0.714 mmol) in a mixture of ethyl acetate (60 ml) and ethanol (20 ml) was treated with 1 atm of hydrogen at 25° C. over 10% palladium on activated carbon (0.10 g) for 2.5 h to give 0.160 g (94% yield) of the title compound as white needles; mp 172–174° C. (ethyl acetate). 1HNMR 400 MHz (CDCl3) δ ppm: 1.47 (3H, t, J=7.3 Hz, CH3), 4.08 (4H, m, 2×CH2), 4.54 (2H, q, J=7.3 Hz, OCH2), 4.72 (2H, s, OCH2), 10.75 (1H, s, OH). Anal. Calcd for C10H12N2O5: C, 50.00; H, 5.03; N, 11.66. Found: C, 50.01; H, 4.95; N, 11.54.

Sources & evidence

ORD record
ord-53f08b2ea99c468782d3961dee1fb842
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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