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

HRID 2172601Notes

Reaction equation

HRID 2172601 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([OH:18])[N:13]=[C:12]2[CH3:19])[CH:5]=1.[CH3:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:20])[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][CH2:21][C:22]3[CH:29]=[CH:28][CH:27]=[C:24]([CH3:25])[CH:23]=3)[N:13]=[C:12]2[CH3:19])[CH:5]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12099m-Xylyl bromideHCID 2855718-Crown-6HCID 1363878053-(4-hydroxy-2-methyl-6-oxo-6H-pyrimidin-1-yl)-4-methyl-benzoic acid methyl ester

Product 1

HCID 866862884-methyl-3-[2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-benzoic acid methyl esterYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Intermediate 2 (460 mg, 1.68 mmol) in N,N-dimethylformamide (2 mL) was added 3-methylbenzyl bromide (0.22 mL, 1.68 mmol), potassium carbonate (350 mg, 2.53 mmol) and 18-crown-6 (40 mg). The slurry was stirred at ambient temperature for one hour. The reaction 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 in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide the alkylated product as a white semi-solid (138 mg, 22% yield). MS (M+H): 379

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe slurry was filtered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified

Sources & evidence

ORD record
ord-75d0745ab3064992b1945e1f91ee0e89
Source dataset
uspto-grants-2015_06
Patent number
US09056110B2

Reaction notes

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