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

HRID 1876871

반응식

HRID 1876871 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-79ac9d46908542dca8074d8397247aa4
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309718B2

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