Triethylamine → HCID 19827483, compound

HRID 1494294Notes

Reaction equation

HRID 1494294 reaction equation
[CH3:1][C:2]([CH3:15])([CH2:13][CH3:14])[C:3]([OH:12])([C:6]1[CH:7]=[N:8][CH:9]=[N:10][CH:11]=1)[C:4]#[CH:5].I[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.C(N(CC)CC)C>C(#N)C>[OH:12][C:3]([C:6]1[CH:11]=[N:10][CH:9]=[N:8][CH:7]=1)([C:2]([CH3:15])([CH3:1])[CH2:13][CH3:14])[C:4]#[C:5][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 707143-IodopyridineHCID 19827487HCID 19827487, compound

Product 1

HCID 19827483HCID 19827483, compoundYield 128%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A stirred mixture of 4,4-dimethyl-3-hydroxy-3-pyrimidin-5-ylhex-1-yne (412 mg, 2 mmol), 3-iodopyridine (412 mg, 2 mmol), triethylamine (300 μl, 2.2 mmol), copper-I-iodide (20 mg), and bis(triphenylphosphine) palladium-II-chloride (20 mg) in dry acetonitrile (5 ml) under nitrogen was heated at 65° C. After 40 minutes, the reaction was cooled and quenched with dilute aqueous hydrochloric acid. The mixture was neutralised with ammonia, extracted with ethyl acetate (3×20 ml), and the organic extracts were combined. Washing with ammonia, water, and brine, drying over magnesium sulphate and concentration under reduced pressure gave yellow crystals (720 mg). Recrystallisation from ethyl acetate gave the desired product of melting point 170.5°-171.5° C.

Workup

  1. temperaturethe reaction was cooled
  2. customquenched with dilute aqueous hydrochloric acid
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. washWashing with ammonia, water, and brine
  5. dry with materialdrying over magnesium sulphate and concentration under reduced pressure

Sources & evidence

ORD record
ord-b5ee302be367484dba590ee57d81db49
Source dataset
uspto-grants-1991_06
Patent number
US05026418

Reaction notes

Loading…