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Ammonium Carbonate → 2-Amino-4-(3-chlorophenyl)-6-methyl-1,4-dihydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide

HRID 24623
Notes
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Reaction equation

HRID 24623 reaction equation
[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][CH2:9][NH:10][C:11]([C:13]2[CH:14]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[N:15]=[C:16](OC)[NH:17][C:18]=2[CH3:19])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[NH4+:39].[NH4+].C([O-])(=O)C.[NH4+]>C(O)C.C(OCC)(=O)C>[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][CH2:9][NH:10][C:11]([C:13]2[CH:14]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[N:15]=[C:16]([NH2:39])[NH:17][C:18]=2[CH3:19])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 517111Ammonium CarbonateHCID 517165Ammonium AcetateHCID 865860254-(3-Chlorophenyl)-2-methoxyl-6-methyl-1,4-dihydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide

Product 1

HCID 207588772-Amino-4-(3-chlorophenyl)-6-methyl-1,4-dihydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

111 mg (0.234 mmol) of 4-(3-chlorophenyl)-2-methoxyl-6-methyl-1,4-dihydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide was dissolved in 5 ml of ethanol. 67.4 mg (0.702 mmol) of ammonium carbonate and 11.8 mg (0.187 mmol) of ammonium acetate were added to the obtained solution, and they were stirred at 80° C. for 2 days. The reaction mixture was diluted with ethyl acetate. An insoluble matter thus formed was filtered out, and the filtrate was concentrated under reduced pressure. The residue was purified by the basic silica gel chromatography (100% dichloromethane) to obtain the title compound.

Workup

  1. customAn insoluble matter thus formed
  2. filtrationwas filtered out
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by the basic silica gel chromatography (100% dichloromethane)

Sources & evidence

ORD record
ord-7af937a590974f16ad36907baa32ed2e
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06855716B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes