HCID 59646781, compound → HCID 54735192, compound

HRID 1365753Notes

Reaction equation

HRID 1365753 reaction equation
C([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([NH:24][CH2:25][C:26]1[S:30][C:29]([CH3:31])=[N:28][CH:27]=1)=[O:23])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]([C:13]([CH3:20])([CH3:21])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([NH:24][CH2:25][C:26]1[S:30][C:29]([CH3:31])=[N:28][CH:27]=1)=[O:23]

Participants

6

Reactant 2

HCID 59646781HCID 59646781, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54735192HCID 54735192, compoundYield 92.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(benzyloxy)-9,9-dimethyl-N-((2-methylthiazol-5-yl)methyl)-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide (0.210 g, 0.477 mmol) in a mixture of ethyl acetate (200 ml) and ethanol (50 ml) at 25° C. was hydrogenated over 10% palladium on activated carbon (0.25 g) and under one atmosphere of hydrogen for two hours to give 0.154 g (92% yield) of the title compound as white crystals; mp 245° C. (ethanol). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.60 (6H, s, 2×CH3), 2.71 (3H, s, CH3), 4.04 (4H, s, 2×CH2), 4.76 (2H, d, J=6.1 Hz, NCH2), 7.57 (1H, s, CH), 7.82 (1H, broad t, NH), 11.83 (1H, s, OH). Anal. Calcd for C15H18N4O4S: C 51.41; H, 5.17; N, 15.99; Found: C, 51.47; H, 5.29; N, 15.76.

Sources & evidence

ORD record
ord-675c30d64a8341b8931a5d8ef1ab5fb6
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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