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

HRID 1257838

反応式

HRID 1257838 の反応式
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

参加物

9

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3b611d1a6d0d4d738a3a0276fd1b433c
出典データセット
uspto-grants-2013_06
特許番号
US08461330B2

関連ノート

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