Water → HCID 14648843, compound

HRID 1164717Notes

Reaction equation

HRID 1164717 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([OH:29])[C:19]=2[C:20]([O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[O:21])[N:6]=1.[Cl:30][C:31]1[CH:36]=[C:35]([O:37][CH3:38])[N:34]=[C:33](S(C)(=O)=O)[N:32]=1.O>C1COCC1>[Cl:30][C:31]1[CH:36]=[C:35]([O:37][CH3:38])[N:34]=[C:33]([O:29][C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([O:13][C:7]3[N:6]=[C:5]([O:4][CH3:3])[CH:10]=[C:9]([O:11][CH3:12])[N:8]=3)[C:19]=2[C:20]([O:22][CH2:23][CH2:24][Si:25]([CH3:27])([CH3:26])[CH3:28])=[O:21])[N:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 137292254-Chloro-2-(methanesulfonyl)-6-methoxypyrimidineHCID 14648842HCID 14648842, compound

Product 1

HCID 14648843HCID 14648843, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (0.4 g, purity: 60%) was suspended in 50 ml of THF. To this suspension, trimethylsilylethyl 6-(4,6-dimethoxypyrimidin-2-yl)oxysalicylate (3.0 g) was added, and the mixture was stirred at room temperature for 30 minutes. To this mixture, 4-chloro-6-methoxy-2-methylsulfonylpyrimidine (1.8 g) was added, and the mixture was stirred at room temperature for further 12 hours. After completion of the reaction, water was added thereto, and the mixture was extracted with ethyl ether. The ethyl ether layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The crude extract thus obtained was purified by silica gel column chromatography to obtain the above identified compound as a slightly yellow liquid (4.0 g).

Workup

  1. stirringthe mixture was stirred at room temperature for further 12 hours
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl ether
  4. dry with materialThe ethyl ether layer was dried over anhydrous magnesium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. extractionThe crude extract thus
  7. customobtained
  8. customwas purified by silica gel column chromatography
  9. customto obtain the

Sources & evidence

ORD record
ord-bb5a177b201f4d73a007625c66f30d11
Source dataset
uspto-grants-1990_03
Patent number
US04906285

Reaction notes

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