N-[3,5-bis(trifluoromethyl)benzyl]-N-[3-(t-butoxycarbonylamino)propyl]-4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid amide → N-[3,5-bis(trifluoromethyl)benzyl]-N-(3-aminopropyl)-4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid amide hydrochloride

HRID 1829639Notes

Reaction equation

HRID 1829639 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][N:7]([CH2:20][CH2:21][CH2:22][NH:23]C(OC(C)(C)C)=O)[C:8]([C:10]1[C:11]([Cl:19])=[N:12][C:13]([S:17][CH3:18])=[N:14][C:15]=1[Cl:16])=[O:9]>C(OCC)(=O)C.Cl>[ClH:16].[F:38][C:2]([F:1])([F:39])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][N:7]([CH2:20][CH2:21][CH2:22][NH2:23])[C:8]([C:10]1[C:11]([Cl:19])=[N:12][C:13]([S:17][CH3:18])=[N:14][C:15]=1[Cl:16])=[O:9]

Participants

3

Reactant 1

HCID 21030672N-[3,5-bis(trifluoromethyl)benzyl]-N-[3-(t-butoxycarbonylamino)propyl]-4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid amide

Product 1

HCID 86599717N-[3,5-bis(trifluoromethyl)benzyl]-N-(3-aminopropyl)-4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid amide hydrochlorideYield 199%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

3 mol/L hydrogen chloride-ethyl acetate (20 mL) was added to N-[3,5-bis(trifluoromethyl)benzyl]-N-[3-(t-butoxycarbonylamino)propyl]-4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid amide (Compound of Reference Example 4; 8.23 g) while the solution was chilled on an ice bath. The reaction mixture was stirred for 1 hour and then another 1 hour at room temperature. Subsequently, the solvent was removed to obtain N-[3,5-bis(trifluoromethyl)benzyl]-N-(3-aminopropyl)-4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid amide hydrochloride (7.35 g, 100%).

Workup

  1. temperaturewas chilled on an ice bath
  2. customanother 1 hour
  3. customat room temperature
  4. customSubsequently, the solvent was removed

Sources & evidence

ORD record
ord-f4433cd8aeee4830b8e056d819810579
Source dataset
uspto-grants-2006_06
Patent number
US07064119B2

Reaction notes

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