Toluene → 3-{3-[6-(2-Methoxy-phenyl)-pyrimidin-4-yl]-ureido}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1020071Notes

Reaction equation

HRID 1020071 reaction equation
C(O[C:4](=[O:20])[NH:5][C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[N:9]=[CH:8][N:7]=1)C.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][CH2:31][CH:30]([NH2:34])[CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C1(C)C=CC=CC=1>O>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][CH2:31][CH:30]([NH:34][C:4]([NH:5][C:6]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][CH3:19])[N:9]=[CH:8][N:7]=2)=[O:20])[CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 1140TolueneHCID 5458091-BOC-3-AminopiperidineHCID 59509103[6-(2-Methoxy-phenyl)-pyrimidin-4-yl]-carbamic acid ethyl ester

Product 1

HCID 595091183-{3-[6-(2-Methoxy-phenyl)-pyrimidin-4-yl]-ureido}-piperidine-1-carboxylic acid tert-butyl esterYield 85.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-carbamic acid ethyl ester (XL) (0.32 g, 1.1 mmol), 3-amino-piperidine-1-carboxylic acid tert-butyl ester (XLI) (0.23 g, 1.1 mmol) and toluene (4 ml) was subjected to microwave conditions at 120° C. and 100 psi pressure for 10 min. The reaction was monitored by TLC. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to provide 0.40 g of 3-{3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-ureido}-piperidine-1-carboxylic acid tert-butyl ester (XLII).

Workup

  1. customat 120° C.
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e10bc42d21c14a8c9a1412d35ba3b27f
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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