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

HRID 275247노트

반응식

HRID 275247 반응식
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]

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 6327Methyl Chloride용매HCID 6569Methyl Ethyl Ketone용매HCID 11430Potassium Carbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e39863dc35fa43ecb43443a514dbd6e1
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05393459

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