Dichloromethane → 4-[4-Methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyrimidine-2-carboxylic acid

HRID 873548Notes

Reaction equation

HRID 873548 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([C:17]([O:19]C)=[O:18])[N:12]=2)=[C:7]([CH3:21])[C:6]=1[CH:22]1[C:35]2[C:34](=[O:36])[CH2:33][C:32]([CH3:38])([CH3:37])[CH2:31][C:30]=2[O:29][C:28]2[CH2:27][C:26]([CH3:40])([CH3:39])[CH2:25][C:24](=[O:41])[C:23]1=2.ClCCl.CCCCCC>C1COCC1.CO>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([C:17]([OH:19])=[O:18])[N:12]=2)=[C:7]([CH3:21])[C:6]=1[CH:22]1[C:35]2[C:34](=[O:36])[CH2:33][C:32]([CH3:37])([CH3:38])[CH2:31][C:30]=2[O:29][C:28]2[CH2:27][C:26]([CH3:40])([CH3:39])[CH2:25][C:24](=[O:41])[C:23]1=2

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 14798Sodium HydroxideHCID 117700535Methyl 4-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyrimidine-2-carboxylate

Product 1

HCID 1177005224-[4-Methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyrimidine-2-carboxylic acidYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1 M aqueous solution of sodium hydroxide (466 μL, 0.466 mol) was added to a solution of the methyl 4-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyrimidine-2-carboxylate obtained in Example 75-3 (206 mg, 0.388 mmol) in THF (0.5 mL) and methanol (0.5 mL) at room temperature. The mixture thus obtained was stirred at the same temperature as above for 15 minutes. Thereafter, the solvent was distilled away under reduced pressure, and water was then added to the residue. The mixed solution was washed with diethyl ether, and 1 M-hydrochloric acid was then added to the water layer thus obtained, so that it was converted to an acidic aqueous solution. The resulting solution was extracted with ethyl acetate twice. The organic layer thus obtained was washed with brine, and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the residue thus obtained was then solidified with dichloromethane and hexane to obtain the title compound (158 mg, yield: 79%).

Workup

  1. customThe mixture thus obtained
  2. distillationThereafter, the solvent was distilled away under reduced pressure, and water
  3. additionwas then added to the residue
  4. washThe mixed solution was washed with diethyl ether, and 1 M-hydrochloric acid
  5. additionwas then added to the water layer
  6. customthus obtained, so that it
  7. extractionThe resulting solution was extracted with ethyl acetate twice
  8. customThe organic layer thus obtained
  9. washwas washed with brine
  10. dry with materialwas then dried over anhydrous sodium sulfate
  11. distillationThe solvent was distilled away under reduced pressure
  12. customthe residue thus obtained

Sources & evidence

ORD record
ord-c5aa1552aeb84abebf9b7b7060828f36
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

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