Water → 3-[4-(2-chloro-5-methoxypyrimidin-4-yl)-1H-pyrazol-1-yl]-3-cyclopropylpropanenitrile

HRID 1876896ノート

反応式

HRID 1876896 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([O:9][CH3:10])=[CH:4][N:3]=1.[CH:11]1([CH:14]([N:18]2[CH:22]=[C:21](B3OC(C)(C)C(C)(C)O3)[CH:20]=[N:19]2)[CH2:15][C:16]#[N:17])[CH2:13][CH2:12]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:21]2[CH:20]=[N:19][N:18]([CH:14]([CH:11]3[CH2:13][CH2:12]3)[CH2:15][C:16]#[N:17])[CH:22]=2)[C:5]([O:9][CH3:10])=[CH:4][N:3]=1

参加物

8

反応物 5

HCID 962WaterHCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 6014012,4-Dichloro-5-methoxypyrimidineHCID 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 866373033-[4-(2-chloro-5-methoxypyrimidin-4-yl)-1H-pyrazol-1-yl]-3-cyclopropylpropanenitrile収率 23.43%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2,4-dichloro-5-methoxypyrimidine (from Aldrich Chemicals, 1.47 g, 0.00821 mol), 3-cyclopropyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propanenitrile (from example 177 step 1, 2.34 g, 0.00815 mol), tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.0005 mol), and potassium phosphate (5.2 g, 0.025 mol) in 1,4-dioxane (20 mL, 0.3 mol) and water (2 mL, 0.1 mol) was heated at 100° C. overnight. After cooling to room temperature, the mixture was dilute with AcOEt, washed with water, brine, dried over MgSO4, concentrated. The residue was purified on silica gel, eluting with 0 to 60%, to give the desired product (580 mg, 23.43%). LCMS (M+H) 304.3

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 60%

出典と根拠

ORDレコード
ord-14b848bfdcea4116a5612e4be3f84866
出典データセット
uspto-grants-2012_11
特許番号
US08309718B2

反応ノート

読み込み中…