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m-Chloroperbenzoic acid → 4-(3-chloro-4-methoxybenzyloxy)-2-(methylsulfinyl)-N-(4-fluorobenzyl)pyrimidine-5-carboxamide

HRID 874514
Notes
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Reaction equation

HRID 874514 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][O:6][C:7]1[C:12]([C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:14])=[CH:11][N:10]=[C:9]([S:24][CH3:25])[N:8]=1.C1C=C(Cl)C=C(C(OO)=[O:39])C=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][O:6][C:7]1[C:12]([C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:14])=[CH:11][N:10]=[C:9]([S:24]([CH3:25])=[O:39])[N:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 901694574-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(4-fluorobenzyl)pyrimidine-5-carboxamide

Product 1

HCID 712350754-(3-chloro-4-methoxybenzyloxy)-2-(methylsulfinyl)-N-(4-fluorobenzyl)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(4-fluorobenzyl)pyrimidine-5-carboxamide (206 mg, 0.46 mmol) was dissolved in 20 mL dichloromethane, m-CPBA (80 mg, 0.46 mmol) was added and reacted at room temperature for 12 h, the reaction solution was washed with water after the reaction is complete, extracted with dichloromethane, the organic layer was dried, dried by rotation to obtain yellow solid, the product was directly used in the next reaction without purification.

Workup

  1. customreacted at room temperature for 12 h
  2. washthe reaction solution was washed with water after the reaction
  3. extractionextracted with dichloromethane
  4. customthe organic layer was dried
  5. customdried by rotation
  6. customto obtain yellow solid
  7. customthe product was directly used in the next reaction without purification

Sources & evidence

ORD record
ord-161cd8b59ffc4f6dafa0dd19d36b8439
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08980904B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes