Potassium Carbonate → HCID 118105706, compound

HRID 1496970Notes

Reaction equation

HRID 1496970 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][N:29]([C:32]([O-:34])=[O:33])[CH2:28][CH2:27]2)=[CH:22][C:21]=1[O:35][CH3:36]>C(O)CCC>[C:5]([O:33][C:32]([N:29]1[CH2:30][CH2:31][N:26]([C:23]2[CH:24]=[CH:25][C:20]([NH:19][C:6]3[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)=[C:21]([O:35][CH3:36])[CH:22]=2)[CH2:27][CH2:28]1)=[O:34])([CH3:9])([CH3:6])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 131734195HCID 131734195, compound

Product 1

HCID 118105706HCID 118105706, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

2,4-dichloro-5-(trifluoromethyl)pyrimidine (800 mg) and potassium carbonate (510 mg) were dissolved in n-butanol (15 ml), dropwisely added with a reaction solution, in which 4-(4-amino-3-methoxyphenyl)piperazin-1-carboxylate (1.13 g) was dissolved in n-butanol (5 ml), and stirred at room temperature overnight. Then, the mixture was distilled under reduced pressure to remove the solvent, added with ethyl acetate, and washed with saturated brine. The washed organic layer was dried with sodium sulfate, and concentrated under reduced pressure. The concentrated mixture was purified by column chromatography to obtain a target compound (430 mg).

Workup

  1. distillationThen, the mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. additionadded with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialThe washed organic layer was dried with sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrated mixture was purified by column chromatography

Sources & evidence

ORD record
ord-532c4d6f1c34487484eca7b47bbc2284
Source dataset
uspto-grants-2015_12
Patent number
US09199944B2

Reaction notes

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