Chlorosuccinimide → 3-[5-chloro-2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid methyl ester

HRID 2172602Notes

Reaction equation

HRID 2172602 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])[CH:21]=3)[N:13]=[C:12]2[CH3:27])[CH:5]=1.[Cl:29]N1C(=O)CCC1=O>C(O)(C)C.ClC(Cl)C(O)=O>[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]([Cl:29])=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=3)[N:13]=[C:12]2[CH3:27])[CH:5]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 866862884-methyl-3-[2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-benzoic acid methyl ester

Product 1

HCID 866862893-[5-chloro-2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid methyl esterYield 96%

Reagents, catalysts & solvents 2

HCID 6597Dichloroacetic AcidCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-methyl-3-[2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-benzoic acid methyl ester from Step A (218 mg, 0.58 mmol) in isopropanol (2 mL) was added N-chlorosuccinimide (84 mg, 0.63 mmol) and 2 drops of dichloroacetic acid. The solution was heated at 60° C. for two hours. The solution was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the chlorinated product as a light yellow oil (230 mg, 78%). MS (M+H): 413

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe slurry was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fe035b0103084243a6c14f8ab6a9ce9b
Source dataset
uspto-grants-2015_06
Patent number
US09056110B2

Reaction notes

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