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

HRID 77833

반응식

HRID 77833 반응식
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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-8b516c37d4ea4c2baa72aa8bf98345ef
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

연결된 노트

불러오는 중…