2H-Azepin-2-one, 3-aminohexahydro- → 3-(2,5-Dichloropyrimidin-4-ylamino)azepan-2-one

HRID 1897651Notes

Reaction equation

HRID 1897651 reaction equation
[NH2:1][CH:2]1[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:3]1=[O:4].[Cl:10][C:11]1[N:16]=[C:15](Cl)[C:14]([Cl:18])=[CH:13][N:12]=1.C([O-])(O)=O.[Na+]>CO.O>[Cl:10][C:11]1[N:16]=[C:15]([NH:1][CH:2]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:3]2=[O:4])[C:14]([Cl:18])=[CH:13][N:12]=1

Participants

6

Reactant 3

HCID 1024632H-Azepin-2-one, 3-aminohexahydro-HCID 2372592,4,5-TrichloropyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 582551133-(2,5-Dichloropyrimidin-4-ylamino)azepan-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of (±)-α-amino-ε-caprolactam (256 mg, 2.0 mmol), 2,4,5-trichloropyrimidine (366 mg, 2.0 mmol, 1 equiv.) and NaHCO3 (168 mg, 2 mmol, 1 equiv.) in a mixture of MeOH (12 mL) and H2O (6 mL) was stirred at room temperature for 15 h. The resulting precipitate was collected by vacuum filtration and washed with small amounts of MeOH and water, providing the product 3-(2,5-dichloropyrimidin-4-ylamino)azepan-2-one; ESMS m/z 275.0 (M+H+).

Workup

  1. filtrationThe resulting precipitate was collected by vacuum filtration
  2. washwashed with small amounts of MeOH and water

Sources & evidence

ORD record
ord-d236f3eb088b4ae593db7354b9af2812
Source dataset
uspto-grants-2013_08
Patent number
US08519129B2

Reaction notes

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