2,4,5-Trichloropyrimidine → (+/-)-cis-2-(2,5-Dichloropyrimidin-4-ylamino)cyclohexanecarboxamide

HRID 2091930Notes

Reaction equation

HRID 2091930 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:8]([NH2:10])=[O:9].[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([Cl:19])=[CH:14][N:13]=1.C([O-])(O)=O.[Na+]>CO.O.CCOC(C)=O>[Cl:11][C:12]1[N:17]=[C:16]([NH:1][C@H:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]2[C:8]([NH2:10])=[O:9])[C:15]([Cl:19])=[CH:14][N:13]=1

Participants

7

Reactant 3

HCID 2372592,4,5-TrichloropyrimidineHCID 516892Sodium BicarbonateHCID 2724813cis-2-Aminocyclohexanecarboxamide

Product 1

HCID 86647791(+/-)-cis-2-(2,5-Dichloropyrimidin-4-ylamino)cyclohexanecarboxamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (±)-cis-2-aminocyclohexanecarboxamide (28 mg, 0.20 mmol), 2,4,5-trichloropyrimidine (37 mg, 0.20 mmol, 1 equiv.) and NaHCO3 (17 mg, 0.20 mmol, 1 equiv.) in a mixture of MeOH (1.0 mL) and H2O (0.5 mL) is stirred at room temperature for 12 h. The reaction is diluted with EtOAc and washed with water (2×), dried over Na2SO4 and concentrated in vacuo to generate the product (±)-cis-2-(2,5-dichloropyrimidin-4-ylamino)cyclohexanecarboxamide; ESMS m/z 289.1 (M+H+).

Workup

  1. washwashed with water (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d11d90deffc4de2b63a04c1097f3c80
Source dataset
uspto-grants-2013_05
Patent number
US08440681B2

Reaction notes

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