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4-Amino-1-Boc-piperidine → 4-[4-(4-Chloro-benzyl)-6-(1-hydroxy-1-methyl-ethyl)-pyrimidin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 451420
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HRID 451420 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:3]=1.[NH2:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:30]([O:29][C:27]([N:24]1[CH2:25][CH2:26][CH:21]([NH:20][C:2]2[N:3]=[C:4]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH:5]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[N:7]=2)[CH2:22][CH2:23]1)=[O:28])([CH3:33])([CH3:31])[CH3:32]
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참가 물질

8

반응물 4

HCID 12682914-Amino-1-Boc-piperidineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 866567012-[2-Chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-ol

생성물 1

HCID 673420264-[4-(4-Chloro-benzyl)-6-(1-hydroxy-1-methyl-ethyl)-pyrimidin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester수율 30%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
150 °C

실험 절차

To a mixture of 2-[2-chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-ol (500 mg, 1.68 mmol), 4-amino-1-Boc-piperidine (404 mg, 2.02 mmol), sodium tert-butoxide (243 mg, 2.52 mmol) in dioxane (2.5 mL) was added under an argon atmosphere palladium(II) acetate (30 mg, 0.14 mmol) and 2-(dicyclohexylphosphino)biphenyl (94 mg, 0.27 mmol) and the reaction mixture was heated to 150° C. for 30 minutes in a microwave oven. It was diluted with ethyl acetate (15 mL) and washed with water (15 mL) and brine (15 mL). The aqueous layers were extracted with ethyl acetate (15 mL) and dried over sodium sulfate. Purification by chromatography (SiO2, heptane:ethyl acetate=80:20 to 60:40) afforded the title compound (230 mg, 30%) as a light brown oil.

후처리

  1. washwashed with water (15 mL) and brine (15 mL)
  2. extractionThe aqueous layers were extracted with ethyl acetate (15 mL)
  3. dry with materialdried over sodium sulfate
  4. customPurification by chromatography (SiO2, heptane:ethyl acetate=80:20 to 60:40)

출처 및 근거

ORD 기록
ord-3c52f781cb2a42398c98fcbaf3de2e7f
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08486967B2

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