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 41687ノート

反応式

HRID 41687 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1a5538eae8114f16b3a16133cfb52b25
出典データセット
uspto-grants-2013_09
特許番号
US08530667B2

反応ノート

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