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

HRID 874512Notes

Reaction equation

HRID 874512 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:5][O:6][C:7]1[C:12]([C:13]([NH:15][CH2:16][C:17]2[CH: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>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:5][O:6][C:7]1[C:12]([C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=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 712351214-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(pyridin-2-ylmethyl)pyrimidine-5-carboxamide

Product 1

HCID 712351224-(3-chloro-4-methoxybenzyloxy)-2-(methylsulfinyl)-N-(pyridin-2-ylmethyl)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(pyridin-2-ylmethyl)pyrimidine-5-carboxamide (180 mg, 0.42 mmol) was dissolved in 20 ml of dichloromethane, m-CPBA (80 mg, 0.46 mmol) was added and reacted at room temperature for 12 h, washed with water after reaction, extracted with dichloromethane, the organic layer was dried, dried by rotation to obtain yellow solid, and this product was directly used in the next reaction without purification.

Workup

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

Sources & evidence

ORD record
ord-0b6beac62e3b44dea5cd5d781ce01305
Source dataset
uspto-grants-2015_03
Patent number
US08980904B2

Reaction notes

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