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Acetic Acid → 3-Phenylpropyl 4-(3,4-dichlorophenyl)-2-(4-methylphenyl)-6-[(2-(1-piperidinyl)ethoxy)methyl]-1,4-dihydropyrimidine-5-carboxylate

HRID 324786
Notes
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Reaction equation

HRID 324786 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH:30]=O.Cl.[C:37]1([CH3:46])[CH:42]=[CH:41][C:40]([C:43]([NH2:45])=[NH:44])=[CH:39][CH:38]=1.C(O)(=O)C>CN(C)C=O>[Cl:26][C:27]1[CH:28]=[C:29]([CH:30]2[C:12]([C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:14])=[C:11]([CH2:10][O:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[NH:45][C:43]([C:40]3[CH:41]=[CH:42][C:37]([CH3:46])=[CH:38][CH:39]=3)=[N:44]2)[CH:32]=[CH:33][C:34]=1[Cl:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 227103,4-DichlorobenzaldehydeHCID 1227534-Methylbenzene-1-carboximidamide hydrochlorideHCID 220055123-Phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate

Product 1

HCID 220055333-Phenylpropyl 4-(3,4-dichlorophenyl)-2-(4-methylphenyl)-6-[(2-(1-piperidinyl)ethoxy)methyl]-1,4-dihydropyrimidine-5-carboxylate
Yield 0.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate (7.9 g, 22.7 mmol), 3,4-dichlorobenzaldehyde (4.0 g, 22.7 mmol), p-toluamidine hydrochloride (3.87 g, 22.7 mmol) and glacial acetic acid (1.3 mL, 22.7 mmol) was stirred in N,N-dimethylformamide (40 ml) for 2 days at room temperature and then heated to 60° C. for 7 days. The DMF was removed in vacuo and ethyl acetate was added to the residue. The precipitate was removed by filtration and the filtrate was washed with water, sodium hydrogen carbonate solution and brine, dried and evaporated to yield an oil. The oil was further purified by flash chromatography and RP-HPLC to give the title compound (45 mg) as an oil. Electrospray MS m/z 620/622 [M+H]+.

Workup

  1. customThe DMF was removed in vacuo and ethyl acetate
  2. additionwas added to the residue
  3. customThe precipitate was removed by filtration
  4. washthe filtrate was washed with water, sodium hydrogen carbonate solution and brine
  5. customdried
  6. customevaporated
  7. customto yield an oil
  8. customThe oil was further purified by flash chromatography and RP-HPLC

Sources & evidence

ORD record
ord-724a4bcc26cb429cb1cdfa52a6677272
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06218538B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes