Methylamine → Benzyl 4-[3-(methylcarbonylmethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate

HRID 20235

Reaction equation

HRID 20235 reaction equation
[CH3:1]CN=C=NCCCN(C)C.[CH2:12]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([N:28]2[CH2:33][CH2:32][CH2:31][N:30]([CH2:34][C:35](O)=[O:36])[C:29]2=[O:38])[CH2:24][CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN.C1C=CC2N(O)N=NC=2C=1>C1COCC1.C1COCC1.ClCCl>[CH3:1][C:35]([CH2:34][N:30]1[CH2:31][CH2:32][CH2:33][N:28]([CH:25]2[CH2:24][CH2:23][N:22]([C:20]([O:19][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:21])[CH2:27][CH2:26]2)[C:29]1=[O:38])=[O:36]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 22137504[3-{1-[(Benzyloxy)carbonyl]piperidin-4-yl}-2-oxotetrahydropyrimidin-1(2H)-yl]acetic acid

Product 1

HCID 68420143Benzyl 4-[3-(methylcarbonylmethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylateYield 100.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

WSC (0.39 g) was added to a solution of [3-{1-[(benzyloxy)carbonyl]piperidin-4-yl}-2-oxotetrahydropyrimidin-1(2H)-yl]acetic acid (0.70 g) obtained in Example 36a), a solution of methylamine in THF (1.85 mL) and HOBt (0.31 g) in THF/dichloromethane (1/1, 30 mL) and the mixture was stirred at room temperature overnight. The solvent were distilled off under reduced pressure, and the residue was diluted with ethyl acetate. The mixture was washed with an aqueous saturated sodium bicarbonate solution and saturated saline solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified with basic silica gel column chromatography (ethyl acetate) to obtain the title compound (0.70 g, 97%) as a white powder.

Workup

  1. distillationThe solvent were distilled off under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe mixture was washed with an aqueous saturated sodium bicarbonate solution and saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with basic silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b2e4d098bba64bbdb603aa0c7363737c
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Linked notes

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