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

HRID 275247ノート

反応式

HRID 275247 の反応式
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]

参加物

9

反応物 5

HCID 525Malic AcidHCID 9260PyrimidineHCID 123472(Diethylamino)sulfur trifluorideHCID 20087472HCID 20087472、化合物HCID 1356171524-(5-Heptyl-2-pyrimidinyl)phenol

生成物 1

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

試薬・触媒・溶媒 3

HCID 6327Methyl Chloride溶媒HCID 6569Methyl Ethyl Ketone溶媒HCID 11430Potassium Carbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e39863dc35fa43ecb43443a514dbd6e1
出典データセット
uspto-grants-1995_02
特許番号
US05393459

反応ノート

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