N-bromobutanimide → 3-[5-bromo-2-methyl-4-(6-methyl-pyridin-2-ylmethoxy)-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid methyl ester

HRID 2172621Notes

Reaction equation

HRID 2172621 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=3)[N:13]=[C:12]2[CH3:27])[CH:5]=1.[Br:29]N1C(=O)CCC1=O>ClCCl>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[C:15]([Br:29])=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=3)[N:13]=[C:12]2[CH3:27])[CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 866862974-methyl-3-[2-methyl-4-(6-methyl-pyridin-2-ylmethoxy)-6-oxo-6H-pyrimidin-1-yl]-benzoic acid methyl ester

Product 1

HCID 866862983-[5-bromo-2-methyl-4-(6-methyl-pyridin-2-ylmethoxy)-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid methyl esterYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-3-[2-methyl-4-(6-methyl-pyridin-2-ylmethoxy)-6-oxo-6H-pyrimidin-1-yl]-benzoic acid methyl ester from Step A (122 mg, 0.32 mmol) in dichloromethane (2 mL) was added N-bromosuccinimide (57 mg, 0.32 mmol). The solution was stirred at ambient temperature for two hours. The solution was washed with water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the brominated product as colorless oil (148 mg, quantitative yield). MS (M, M+2): 458, 460

Workup

  1. washThe solution was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe slurry was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5b3bdad50aef4b01af29a1c741ad8fbc
Source dataset
uspto-grants-2015_06
Patent number
US09056110B2

Reaction notes

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