m-Chloroperbenzoic acid → Avanafil Impurity K

HRID 2200864Notes

Reaction equation

HRID 2200864 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:5][NH:6][C:7]1[C:12]([C:13]([NH:15][CH2:16][C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:14])=[CH:11][N:10]=[C:9]([S:23][CH3:24])[N:8]=1.C1C=C(Cl)C=C(C(OO)=[O:38])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:5][NH:6][C:7]1[C:12]([C:13]([NH:15][CH2:16][C:17]2[N:18]=[CH:19][CH:20]=[CH:21][N:22]=2)=[O:14])=[CH:11][N:10]=[C:9]([S:23]([CH3:24])=[O:38])[N:8]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 73505986HCID 73505986, compound

Product 1

HCID 86342163Avanafil Impurity KYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In DCM (5 mL) was dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide (150 mg, 0.35 mmol). m-CPBA (3-chloroperbenzoic acid, 110 mg, 0.64 mmol) was added at 0° C. The reaction was conducted for 30 min at ambient temperature. Then the reaction mixture was washed with water and extracted with DCM. The organic phase was dried, and the solvent was removed by rotary evaporation. Purification was performed by silica gel column chromatography (DCM/methanol=50/1) to give solid 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulphinyl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide (100 mg, 64% yield).

Workup

  1. washThen the reaction mixture was washed with water
  2. extractionextracted with DCM
  3. customThe organic phase was dried
  4. customthe solvent was removed by rotary evaporation
  5. customPurification

Sources & evidence

ORD record
ord-11c4206659cb4c66b0f441158fc6f874
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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