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

HRID 2172616Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-methyl-3-[2-methyl-4-(2-methyl-thiazol-4-ylmethoxy)-6-oxo-6H-pyrimidin-1-yl]-benzoic acid methyl ester from Step A, of Example 11 (120 mg, 0.31 mmol) in isopropanol (1.5 mL) was added N-chlorosuccinimide (46 mg, 0.34 mmol) and 2 drops of dichloroacetic acid. The solution was heated at 60° C. for three hours. The solution was allowed to cool and 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 colorless oil (125 mg, 96%). MS (M+H): 420

Workup

temperatureto cool
concentrationconcentrated in vacuo
customthe residue was partitioned between ethyl acetate and water
washThe organic layer was washed with water and brine
dry with materialdried over magnesium sulfate
filtrationThe slurry was filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-9a922d51f7a944358b12612a395e16b0
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056110B2

Reaction notes

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