Guanidine → {1-[4-(2-Amino-5-phenyl-pyrimidin-4-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester

HRID 2362166노트

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HRID 2362166 반응식
[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20]N(C)C)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[NH2:32][C:33]([NH2:35])=[NH:34].CO[Na]>CN(C=O)C.CC(=O)OCC>[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:20][N:32]=[C:33]([NH2:35])[N:34]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 3520GuanidineHCID 66719111HCID 66719111, 화합물HCID 178418582HCID 178418582, 화합물

생성물 1

HCID 66823192{1-[4-(2-Amino-5-phenyl-pyrimidin-4-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester수율 70%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To a solution of compound 1 (3 g, 7.2 mmol) and guanidine (2 g, 35 mmol) in DMF (15 mL) was added MeONa (1.8 g, 35 mmol) and the mixture was heated to 100° C. and stirred for 4 h. The solution was cooled to r.t. and diluted with 80 mL of EA. The organic phase was washed with 0.1N HClaq and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel column chromatography to give 2.1 g of 5-1 as a yellow solid.

후처리

  1. temperatureThe solution was cooled to r.t.
  2. washThe organic phase was washed with 0.1N HClaq and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-696a31ff9ca34d578fd78eef1034b599
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691825B2

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