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Triethylamine → Ethyl 5-(benzyloxy)-1-(methylsulfonyl)-2-(4-((methylsulfonyloxy)methyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

HRID 1093118
Notes
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Reaction equation

HRID 1093118 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[NH:13][C:12]([N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][OH:23])[CH2:18][CH2:17]2)=[N:11][C:10]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31].CCN(CC)CC>C1COCC1>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([S:30]([CH3:29])(=[O:32])=[O:31])[C:12]([N:16]2[CH2:17][CH2:18][CH:19]([CH2:22][O:23][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:20][CH2:21]2)=[N:11][C:10]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 136061319Ethyl 5-(benzyloxy)-2-(4-(hydroxymethyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Product 1

HCID 57904840Ethyl 5-(benzyloxy)-1-(methylsulfonyl)-2-(4-((methylsulfonyloxy)methyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylateYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of ethyl 5-(benzyloxy)-2-(4-(hydroxymethyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate (0.814 g, 2.1 mmol) in THF (20 mL) was added methanesulfonyl chloride (0.327 mL, 4.20 mmol) followed by Et3N (0.732 mL, 5.25 mmol). The resulting mixture was stirred at room temperature for 2.5 h (white solids precipitated out over the reaction time). The mixture was diluted with ethyl acetate (50 mL) and washed with water followed by brine. The organic phase was dried (Na2SO4), filtered and concentrated to give the title compound as an amber oil (1.1320 g, 99% yield). 1H NMR (500 MHz, CDCl3) δ: 7.44 (2H, d, J=7.32 Hz), 7.39-7.32 (3H, m), 4.98 (2H, s), 4.67-4.64 (2H, m), 4.35 (2H, q, J=7.1 Hz), 4.09 (2H, d, J=6.4 Hz), 3.46 (3H, s), 3.02 (3H, s), 2.91 (2H, td, J=12.9, 2.4 Hz), 2.08-2.00 (1H, m), 1.86-1.84 (2H, m), 1.35-1.28 (5H, m). LCMS (M+H) calcd for C22H30N3O9S2: 544.14; found: 544.30.

Workup

  1. customprecipitated out over the reaction time)
  2. additionThe mixture was diluted with ethyl acetate (50 mL)
  3. washwashed with water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ad40a6e587e445c48b965c097c0e9d1b
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129398B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes