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3-Methylbut-1-yne → 6-Methoxy-4-(3-methylbut-1-ynyl)pyridin-3-amine

HRID 43261
Notes
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Reaction equation

HRID 43261 reaction equation
I[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[CH:4][C:3]=1[NH2:10].[CH3:11][CH:12]([CH3:15])[C:13]#[CH:14]>CCN(CC)CC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:9][O:8][C:6]1[N:5]=[CH:4][C:3]([NH2:10])=[C:2]([C:14]#[C:13][CH:12]([CH3:15])[CH3:11])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 690193-Methylbut-1-yneHCID 110212874-Iodo-6-methoxypyridin-3-amine2×

Product 1

HCID 580250656-Methoxy-4-(3-methylbut-1-ynyl)pyridin-3-amine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compound
Catalyst
HCID 8471TriethylamineSolvent

Procedure

To a solution of 4-iodo-6-methoxypyridin-3-amine (Compound 3, 845 mg, 3.4 mmol) in Et3N (12 ml) in a re-sealable pressure tube was added Pd(PPh3)2Cl2 (24 mg, 0.034 mmol), CuI (7.0 mg, 0.034 mmol), and 3-methyl-1-butyne (0.66 ml, 6.8 mmol). The mixture was stirred at room temperature for 20 h and the solvent was removed in vacuo. The residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes) to yield the title compound as beige solid.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-deb59c03055b4bb29d9d3f2aa34398ad
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536339B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes