Malic Acid → 5-Heptyl-2-(4-(2-fluoro-5-oxaoctyloxy)phenyl)pyrimidine

HRID 275247Notes

Reaction equation

HRID 275247 reaction equation
N1C=CC=NC=1.[O:7]1[CH:9]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH3:15])[CH2:8]1.C(O)(=O)C(CC(O)=O)O.[CH2:25]([C:32]1[CH:33]=[N:34][C:35]([C:38]2[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=2)=[N:36][CH:37]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].CCN(S(F)(F)[F:51])CC>C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C.CCl>[CH2:25]([C:32]1[CH:33]=[N:34][C:35]([C:38]2[CH:43]=[CH:42][C:41]([O:7][CH2:8][CH:9]([F:51])[CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH3:15])=[CH:40][CH:39]=2)=[N:36][CH:37]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

9

Reactant 5

HCID 525Malic AcidHCID 9260PyrimidineHCID 123472(Diethylamino)sulfur trifluorideHCID 20087472HCID 20087472, compoundHCID 1356171522-(4Hydroxyphenyl)-5-n-heptylpyrimidine

Product 1

HCID 200874355-Heptyl-2-(4-(2-fluoro-5-oxaoctyloxy)phenyl)pyrimidine

Reagents, catalysts & solvents 3

HCID 6327Methyl ChlorideSolventHCID 6569Methyl Ethyl KetoneSolventHCID 11430Potassium CarbonateSolvent

Procedure

A solution of 0.1 mol of 5-heptyl-2-(4-2-hydroxy-5-oxaoctyloxy)phenyl)pyrimidine (prepared by heating optically active 1,2-epoxy-5-oxaoctane, obtainable from malic acid, with 5-heptyl-2-(p-hydroxyphenyl)pyrimidine in the presence of dry potassium carbonate and methyl ethyl ketone as solvent) in methyl chloride is cooled to -40° C., and 0.11 mol of DAST is added dropwise with exclusion of moisture. The reaction mixture is subsequently stirred at room temperature for 12 hours with slow warming, then hydrolyzed with ice cooling and washed with dilute sodium hydroxide solution and several times with water. After the mixture has been dried over magnesium sulfate, the solvent is removed on a rotary evaporator, and the crude product is purified by chromatography and crystallization, to give optically active 5-heptyl-2-(4-(2-fluoro-5-oxaoctyloxy)phenyl)pyrimidine, C 41 SA (35) I.

Workup

  1. washhydrolyzed with ice cooling and washed with dilute sodium hydroxide solution and several times with water
  2. dry with materialAfter the mixture has been dried over magnesium sulfate
  3. customthe solvent is removed on a rotary evaporator
  4. customthe crude product is purified by chromatography and crystallization

Sources & evidence

ORD record
ord-e39863dc35fa43ecb43443a514dbd6e1
Source dataset
uspto-grants-1995_02
Patent number
US05393459

Reaction notes

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