Acetic Acid → HCID 58786867, compound

HRID 1161944Notes

Reaction equation

HRID 1161944 reaction equation
[C:1]([O:9][C:10]1[C:11]([OH:44])=[N:12][C:13]([C:20]2([CH3:43])[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23][CH2:22][N:21]2[C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])=[N:14][C:15]=1[C:16]([O:18][CH3:19])=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Li+].[CH3:47]OS(OC)(=O)=O.C(O)(=O)C>O1CCOCC1.CCOC(C)=O.O>[C:1]([O:9][C:10]1[C:11](=[O:44])[N:12]([CH3:47])[C:13]([C:20]2([CH3:43])[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])[CH2:23][CH2:22][N:21]2[C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])=[N:14][C:15]=1[C:16]([O:18][CH3:19])=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6497Dimethyl SulfateHCID 62714Lithium hydrideHCID 178499077HCID 178499077, compound

Product 1

HCID 58786867HCID 58786867, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

1-Benzyl 4-tert-butyl 2-[5-(benzoyloxy)-4-hydroxy-6-(methoxycarbonyl)pyrimidin-2-yl]-2-methylpiperazine-1,4-dicarboxylate was added to a suspension of LiH (1.1 eq) in dioxane (7 ml/mmol) at room temperature. The mixture was stirred at 40° C. for 45 min, then dimethylsulfate (1.3 eq) was added and the temperature was raised to 60° C. After 1 h glacial acetic acid (0.1 eq) was added to the reaction mixture, followed by water (7 ml/mmol) and EtOAc (7 ml/mmol). The aqueous layer was separated and extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated. The crude was purified by flash chromatography on silica gel (AcOEt/petroleum ether, 1:4) to separate the title compound A from B (ratio A/B 1.3/1).

Workup

  1. temperaturethe temperature was raised to 60° C
  2. customThe aqueous layer was separated
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude was purified by flash chromatography on silica gel (AcOEt/petroleum ether, 1:4)
  7. customto separate the title compound A from B (ratio A/B 1.3/1)

Sources & evidence

ORD record
ord-ca53125f76bd44978844a19de5f214a0
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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