Sodium hydride → 2-(4-(4-Methyloctoxy)phenyl)-5-n-decylpyrimidine

HRID 1762250Notes

Reaction equation

HRID 1762250 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:12][N:11]=2)=[CH:6][CH:5]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH3:37][CH:38]([CH2:43][CH2:44][CH2:45][CH3:46])[CH2:39][CH2:40][CH2:41]O>CN(C)C=O.C(OCC)C>[CH3:37][CH:38]([CH2:43][CH2:44][CH2:45][CH3:46])[CH2:39][CH2:40][CH2:41][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[CH:12][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:14][N:15]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 85570p-ToluenesulfonateHCID 30159874-Methyl-1-octanolHCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 1

HCID 143246302-(4-(4-Methyloctoxy)phenyl)-5-n-decylpyrimidine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

0.38 g of 55% sodium hydride and 10 ml of dimethylformamide were weighed out and a solution of 2 g of 2-(4-hydroxyphenyl)-5-n-decylpyrimidine in 3 ml of dimethylformamide was added dropwise thereto under ice cooling. After the completion of the addition, the resulting mixture was stirred at room temperature for one hour. Then p-toluene-sulfonate of optically active 4-methyloctanol was added dropwise thereto and the resulting mixture was stirred at 90° C. for two hours. After cooling, the reaction mixture was poured into ice/water, extractd with diethyl ether and dried followed by removal of the solvent. The residue was purified on a silica gel column to thereby give 1.5 g of optically active 2-(4-(4-methyloctoxy)phenyl)-5-n-decylpyrimidine.

Workup

  1. additionAfter the completion of the addition
  2. stirringthe resulting mixture was stirred at 90° C. for two hours
  3. temperatureAfter cooling
  4. customdried
  5. customfollowed by removal of the solvent
  6. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-33aa20a56194473fa31b525325f034ea
Source dataset
uspto-grants-1989_05
Patent number
US04831143

Reaction notes

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