HCID 58739083, compound → HCID 58739067, compound

HRID 720284Notes

Reaction equation

HRID 720284 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][S:23]2(=[O:29])=[O:28])[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12]CC1C=CC=CC=1)=[O:5])[CH3:2].[H][H]>C(O)C.C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][S:23]2(=[O:28])=[O:29])[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[OH:12])=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 58739083HCID 58739083, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58739067HCID 58739067, compoundYield 82.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)-5-benzyloxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (4.05 g, 9.61 mmol) in a mixture of ethanol (250 ml) and ethyl acetate (250 ml) was hydrogenated over 10% palladium on activated carbon (0.9 g) and under 1 atmosphere of hydrogen for 1 h. The catalyst was then filtered and the solvent was evaporated under reduced pressure. Recrystallization of the residue from ethyl acetate gave 2.63 g (82% yield) of the title ester as white crystals; mp 186–189° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.42 (3H, t, J=7.0 Hz, CH3), 1.6–1.63 (1H, m, CH), 2.3–2.6 (3H, m, CH2 and CH), 3.2 (1H, m, CH), 3.55–3.75 (2H, m, CH2), 3.65 (3H, s, NCH3), 3.95–4.05 (1H, m, CH), 4.44 (2H, q, J=7.0 Hz, OCH2). HRMS (FAB POS) calculated for C12H18N3O6S [M+H+]: 332.091632. found: 332.092342.

Workup

  1. filtrationThe catalyst was then filtered
  2. customthe solvent was evaporated under reduced pressure
  3. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-ad176e4cf2aa4a51a65cab3a54aab65e
Source dataset
uspto-grants-2006_11
Patent number
US07135467B2

Reaction notes

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