HCID 57565062, compound → HCID 54680789, compound

HRID 1726885Notes

Reaction equation

HRID 1726885 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[N:27]([CH3:28])[CH2:26][CH2:25][N:13]3[C:14](=[O:24])[C:15]=2[O:16]CC2C=CC=CC=2)=[O:9])=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[N:27]([CH3:28])[CH2:26][CH2:25][N:13]3[C:14](=[O:24])[C:15]=2[OH:16])=[O:9])=[CH:29][CH:30]=1

Participants

6

Reactant 2

HCID 57565062HCID 57565062, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54680789HCID 54680789, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(4-fluorobenzyl)-6-(benzyloxy)-1-methyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamide (0.202 g, 0.495 mmol) in a mixture of ethyl acetate (150 ml) and ethanol (20 ml) at 25° C. was hydrogenated over 10% palladium on activated carbon (50 mg) and under one atmosphere of hydrogen for one hour to give 0.130 g (83% yield) of the title compound as white needles; mp 212° C. (ethyl acetate). 1HNMR 400 MHz (CDCl3) δ (ppm): 2.93 (3H, s, CH3), 3.63 (2H, t, J=8.6 Hz, CH2), 4.14 (2H, t, J=8.6 Hz, CH2), 4.59 (2H, d, J=6.0 Hz, NCH2), 7.07 (2H, m, aromatics), 7.33 (2H, m, aromatics), 7.89 (1H, broad t, NH), 11.57 (1H, s, OH). HRMS (ESI+) calculated for C15H16FN4O3 [M+H+]: 319.1206. found: 319.1191.

Sources & evidence

ORD record
ord-263ead3156274f55b82af01ad02330b5
Source dataset
uspto-grants-2009_02
Patent number
US07494984B2

Reaction notes

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