Sodium Carbonate → 5-[4-(2-Oxo-2-pyrrolidin-1-ylethoxy)phenyl]pyrimidin-2-amine

HRID 500182

반응식

HRID 500182 반응식
C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[CH:16]=[N:17][C:18]([NH2:21])=[N:19][CH:20]=2)O1.Br[C:24]1[CH:38]=[CH:37][C:27]([O:28][CH2:29][C:30]([N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[O:31])=[CH:26][CH:25]=1>O.C(O)C.C1(C)C=CC=CC=1.CCOC(C)=O.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>[O:31]=[C:30]([N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)[CH2:29][O:28][C:27]1[CH:37]=[CH:38][C:24]([C:15]2[CH:20]=[N:19][C:18]([NH2:21])=[N:17][CH:16]=2)=[CH:25][CH:26]=1

참가 물질

9

반응물 3

HCID 10340Sodium CarbonateHCID 7876791-[(4-Bromophenoxy)acetyl]pyrrolidineHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol ester

생성물 1

HCID 672233665-[4-(2-Oxo-2-pyrrolidin-1-ylethoxy)phenyl]pyrimidin-2-amine

시약·촉매·용매 5

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

Sodium carbonate (0.318 g, 3.0 mmol) in water (2.0 mL) was added to a mixture of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (0.221 g, 1.0 mmol), 1-[(4-bromophenoxy)acetyl]pyrrolidine (0.341 g, 1.2 mmol) and tetrakis(triphenylphosphine)palladium (35 mg, 0.03 mmol) in ethanol (1.5 mL) and toluene (1.5 mL). The resulting mixture was heated at 120° C. for 3 h. The mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue (0.29 g) was directly used in next step without further purification. LCMS: (M+H)=299.1.

후처리

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue (0.29 g) was directly used in next step without further purification

출처 및 근거

ORD 기록
ord-fedfaf05f7a944be9a1a0206acd125ee
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767675B2

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