Potassium Phosphate, Tribasic → 4-(5-Methyl-2-methylsulfanyl-pyrimidin-4-yl)-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione

HRID 41687노트

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HRID 41687 반응식
Cl[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[CH:11]12[O:20][CH:17]([CH2:18][CH2:19]1)[CH:16]1[CH:12]2[C:13](=[O:22])[CH2:14][C:15]1=[O:21].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COCCOC>[CH3:8][C:7]1[C:2]([CH:14]2[C:13](=[O:22])[CH:12]3[CH:16]([CH:17]4[O:20][CH:11]3[CH2:19][CH2:18]4)[C:15]2=[O:21])=[N:3][C:4]([S:9][CH3:10])=[N:5][CH:6]=1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 235627084-Chloro-5-methyl-2-(methylthio)pyrimidineHCID 5935195110-Oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione

생성물 1

HCID 687735424-(5-Methyl-2-methylsulfanyl-pyrimidin-4-yl)-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione수율 11.2%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매

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온도
160 °C

실험 절차

A microwave vial is charged with 4-chloro-5-methyl-2-methylsulfanylpyrimidine (174 mg, 1 mmol), 10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione (166 mg, 1 mmol), palladium acetate (12 mg, 0.05 mmol), X-Phos (48 mg, 0.1 mmol) and potassium phosphate (424 mg, 2 mmol). 1,2-dimethoxyethane (3 ml) is added and the reaction heated to 160° C., with stirring, for 30 minutes. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 4-(5-methyl-2-methylsulfanyl-pyrimidin-4-yl)-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione (34 mg).

후처리

  1. additionSilica gel is added to the crude
  2. customreaction mixture
  3. customthe solvent is evaporated under reduced pressure
  4. customthe residue is purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-1a5538eae8114f16b3a16133cfb52b25
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530667B2

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