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

HRID 2091940Notes

Reaction equation

HRID 2091940 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) is stirred at room temperature for 15 h. The resulting precipitate is 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 is collected by vacuum filtration
  2. washwashed with small amounts of MeOH and water

Sources & evidence

ORD record
ord-270d2f19c1144951b5e237c35f65d83c
Source dataset
uspto-grants-2013_05
Patent number
US08440681B2

Reaction notes

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