Sodium hydride → HCID 19102393, compound

HRID 1198377Notes

Reaction equation

HRID 1198377 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:16][CH:15]=3)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].C1(C)C=CC(S(O[CH2:41][CH2:42][CH:43]([C:50]([F:53])([F:52])[F:51])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])(=O)=O)=CC=1>C1COCC1.CN(C)C=O>[F:51][C:50]([F:52])([F:53])[CH:43]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:42][CH2:41][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:16][CH:15]=3)=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 19102388HCID 19102388, compoundHCID 136132498HCID 136132498, compound

Product 1

HCID 19102393HCID 19102393, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 30 ml-round-bottomed flask, a solution of 0.188 g (0.50 mM) of 2-(4-hydroxyphenyl)-5-(4-octyloxyphenyl)pyrimidine in dry THF and 2 ml of dry N,N-dimethylformamide were placed and sufficiently stirred. To the mixture, 40 mg of 60%-sodium hydride was added and 0.183 g (0.50 mM) of (-)-3-trifluoromethylnonyl p-toluene sulfonate was further added dropwise, followed by stirring for 6 hours at 130° C. After the reaction, distilled water was added to the reaction mixture and extracted with ether, followed by drying with anhydrous sodium sulfate and purification by thin-layer chromatography (developing solvent: hexane/ethyl acetate =3/1 (first) and 4/1 (second)) to obtain 0.13 g (0.23 mM) of 2-{4-(3-trifluoromethylnonyloxy)phenyl}-5-(4-octyloxyphenyl)pyrimidine (Yield: 46.0%). ##STR86##

Workup

  1. stirringby stirring for 6 hours at 130° C
  2. customAfter the reaction
  3. distillationdistilled water
  4. additionwas added to the reaction mixture
  5. extractionextracted with ether
  6. dry with materialby drying with anhydrous sodium sulfate and purification by thin-layer chromatography (developing solvent: hexane/ethyl acetate =3/1 (first) and 4/1 (second))

Sources & evidence

ORD record
ord-a5c60a7d7f7e40398221db6af2b09f83
Source dataset
uspto-grants-1994_01
Patent number
US05281362

Reaction notes

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