Trimethylsilylacetylene → 2,6-Pyridinediamine, 3-[2-(trimethylsilyl)ethynyl]-

HRID 77833

反応式

HRID 77833 の反応式
I[C:2]1[C:3]([NH2:9])=[N:4][C:5]([NH2:8])=[CH:6][CH:7]=1.[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12]>[Cu]I.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.CN1CCCC1=O>[CH3:10][Si:11]([C:14]#[C:15][C:2]1[C:3]([NH2:9])=[N:4][C:5]([NH2:8])=[CH:6][CH:7]=1)([CH3:13])[CH3:12]

参加物

6

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 4762183-Iodopyridine-2,6-diamine

生成物 1

HCID 592554712,6-Pyridinediamine, 3-[2-(trimethylsilyl)ethynyl]-収率 60%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

To a mixture of 3-iodo-pyridin-2,6-diamine (20.0 g, 85.2 mmol) described in Manufacturing Example 13-1-1, trimethylsilyl acetylene (24.2 mL, 170 mmol), copper (I) iodide (3.25 g, 17.0 mmol) N,N-diisopropylethylamine (19.1 g, 148 mmol) and N-methylpyrrolidinone (286 mL) was added tetrakis(triphenylphosphine)palladium (0) (9.81 g, 8.52 mmol) under argon atmosphere, which was stirred for 30 minutes at room temperature. The reaction solution was partitioned into water and ethyl acetate. The ethyl acetate layer was washed with water 4 times and dried over sodium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel chromatography (heptane:ethyl acetate=4:1 then 1:1). The solids obtained by concentrating the eluate under a reduced pressure were washed with heptane containing a small amount of ethyl acetate to obtain the title compound (10.5 g, 60.0%).

後処理

  1. customThe reaction solution was partitioned into water and ethyl acetate
  2. washThe ethyl acetate layer was washed with water 4 times
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by NH silica gel chromatography (heptane
  6. customThe solids obtained
  7. concentrationby concentrating the eluate under a reduced pressure
  8. washwere washed with heptane containing a small amount of ethyl acetate

出典と根拠

ORDレコード
ord-8b516c37d4ea4c2baa72aa8bf98345ef
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

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