Potassium Carbonate → 4-[2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-pyrimidin-4-yl]piperazine-1-carboxylic acid tert-butyl ester

HRID 2175062ノート

反応式

HRID 2175062 の反応式
C1(C)C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[K+].[K+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][N:33]=[C:32](Cl)[N:31]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].CC1(C)C(C)(C)OB([C:45]2[CH:54]=[CH:53][C:52]3[C:51]([CH3:56])([CH3:55])[CH2:50][CH2:49][C:48]([CH3:58])([CH3:57])[C:47]=3[CH:46]=2)O1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClCCl.O>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][N:33]=[C:32]([C:54]3[CH:45]=[CH:46][C:47]4[C:48]([CH3:58])([CH3:57])[CH2:49][CH2:50][C:51]([CH3:56])([CH3:55])[C:52]=4[CH:53]=3)[N:31]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 11197306Tert-butyl 4-(2-chloropyrimidin-4-yl)piperazine-1-carboxylateHCID 112439294,4,5,5-Tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolaneHCID 21863594Toluene ethanol

生成物 1

HCID 672484304-[2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-pyrimidin-4-yl]piperazine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

2.6 ml of toluene/ethanol (4:1) and 335 μl of 2N potassium carbonate solution are added to 100 mg (0.33 mmol) of 4-(2-chloropyrimidin-4-yl)piperazine-1-carboxylic acid tert-butyl ester (preparation analogous to US 2005/176722) and 147 mg (0.47 mmol) of 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane. The reaction mixture is degassed a number of times, 16 mg (0.01 mmol) of tetrakis(triphenylphosphine)palladium(0) are added under nitrogen atmosphere, the mixture is treated in an ultrasound bath for 10 min and subsequently irradiated in the microwave at 140° C. for 10 min. Water and dichloromethane are added to the reaction mixture. The organic phase is separated off, and the aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4 and evaporated. The crude product is purified by means of flash chromatography on silica gel.

後処理

  1. additionare added under nitrogen atmosphere
  2. additionthe mixture is treated in an ultrasound bath for 10 min
  3. customsubsequently irradiated in the microwave at 140° C. for 10 min
  4. customThe organic phase is separated off
  5. extractionthe aqueous phase is extracted three times with ethyl acetate
  6. dry with materialThe combined organic phases are dried over Na2SO4
  7. customevaporated
  8. customThe crude product is purified by means of flash chromatography on silica gel

出典と根拠

ORDレコード
ord-4ca1ad7065be40409a1e89e3704ad228
出典データセット
uspto-grants-2015_06
特許番号
US09062015B2

反応ノート

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