Triethylamine → (3S,5S)-benzyl 3-(5-bromo-2-(methylthio)pyrimidin-4-ylamino)-5-methylpiperidine-1-carboxylate

HRID 1916154Notes

Reaction equation

HRID 1916154 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[NH2:11][C@H:12]1[CH2:17][C@H:16]([CH3:18])[CH2:15][N:14]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:13]1.C(N(CC)CC)C>O1CCOCC1>[CH2:22]([O:21][C:19]([N:14]1[CH2:15][C@@H:16]([CH3:18])[CH2:17][C@H:12]([NH:11][C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]([S:8][CH3:9])[N:4]=2)[CH2:13]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2658815-Bromo-4-chloro-2-(methylsulfanyl)pyrimidineHCID 58177434benzyl (3S,5S)-3-amino-5-methylpiperidine-1-carboxylate

Product 1

HCID 58177451(3S,5S)-benzyl 3-(5-bromo-2-(methylthio)pyrimidin-4-ylamino)-5-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-bromo-4-chloro-2-(methylthio)pyrimidine (1.0 g, 4.2 mmol), (3S,5S)-benzyl 3-amino-5-methylpiperidine-1-carboxylate (2.7 g, 8.35 mmol) and triethylamine 1.3 g, 12.5 mmol) in dioxane (50 ml) were stirred for 16 hours. The reaction was concentrated and the residue dissolved in methylene chloride (50 ml) and washed with water. The organic layer was dried and concentrated and purified on a silica gel column with 10-20% ethyl acetate/dichloromethane as solvent to give (3S,5S)-3-(5-bromo-2-methylsulfanyl-pyrimidin-4-ylamino)-5-methyl-piperidine-1-carboxylic acid benzyl ester as a viscous oil. MS (ES+): 452.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue dissolved in methylene chloride (50 ml)
  3. washwashed with water
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. custompurified on a silica gel column with 10-20% ethyl acetate/dichloromethane as solvent

Sources & evidence

ORD record
ord-992c782e4fb94f50b1d4cedba3a752d8
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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