Citric Acid → HCID 15837479, compound

HRID 1871277Notes

Reaction equation

[OH:1][CH:2]([C:7]([O:20][CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH3:28][O:29][C:30]1[N:35]=[C:34](Cl)[CH:33]=[C:32]([O:37][CH3:38])[N:31]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O.O>[CH3:28][O:29][C:30]1[N:35]=[C:34]([O:1][CH:2]([C:7]([O:20][CH3:21])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]([O:5][CH3:6])=[O:4])[CH:33]=[C:32]([O:37][CH3:38])[N:31]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1.15 g (4 mmol) of methyl 2-hydroxy-3-methoxy-3,3-diphenyl-propionate were dissolved in 10 ml of dimethylformamide, and 276 mg (2 mmol) of potassium carbonate were added. Then 524 mg (3 mmol) of 2,6-dimethoxy-4-chloropyrimidine were added, and the mixture was stirred at 100° C. for 6 hours. It was then cautiously hydrolyzed with 10 ml of water, the pH was adjusted to 5 with citric acid and, after extraction with ethyl acetate, the organic phase was washed with water then dried over magnesium sulfate, and the solvent was removed by distillation. The oily residue (1.9 g) was chromatographed on silica gel, resulting in 617 mg of a slightly impure oil.

Workup

extractionafter extraction with ethyl acetate
washthe organic phase was washed with water
dry with materialthen dried over magnesium sulfate
customthe solvent was removed by distillation
customThe oily residue (1.9 g) was chromatographed on silica gel
customresulting in 617 mg of a slightly impure oil

Sources & evidence

ORD record: ord-a403ec19022245a38b98ef9f5a6cbada
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06103732

Reaction notes

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