Potassium Phosphate, Tribasic → 3-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopropylpropanenitrile

HRID 1876871

反応式

HRID 1876871 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH:9]1([CH:12]([N:16]2[CH:20]=[C:19](B3OC(C)(C)C(C)(C)O3)[CH:18]=[N:17]2)[CH2:13][C:14]#[N:15])[CH2:11][CH2:10]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.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>[Cl:1][C:2]1[N:7]=[C:6]([C:19]2[CH:18]=[N:17][N:16]([CH:12]([CH:9]3[CH2:11][CH2:10]3)[CH2:13][C:14]#[N:15])[CH:20]=2)[CH:5]=[CH:4][N:3]=1

参加物

8

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 775312,4-DichloropyrimidineHCID 674580563-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile

生成物 1

HCID 866372933-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopropylpropanenitrile

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2,4-dichloropyrimidine (2.8 g, 0.019 mol), 3-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile (4.50 g, 0.0157 mol), tetrakis(triphenylphosphine)palladium (1.0 g, 0.9 mmol), and potassium phosphate (0.1 g, 0.047 mol) in 1,4-dioxane (50 mL) and water (5 mL) was heated at 100° C. overnight. After cooling to room temperature, the mixture was diluted with EtOAc, washed with water, brine, dried over MgSO4, and concentrated. The residue was purified on silica gel, eluting with 0 to 100% EtOAc in hexanes, to give the desired product as racemic mixture (3.08 g, 71.81%). LCMS (M+H) 274.3.

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel
  6. washeluting with 0 to 100% EtOAc in hexanes

出典と根拠

ORDレコード
ord-79ac9d46908542dca8074d8397247aa4
出典データセット
uspto-grants-2012_11
特許番号
US08309718B2

関連ノート

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