Triethylamine → HCID 22597426, compound

HRID 1760215Notes

Reaction equation

HRID 1760215 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.C(N(CC)CC)C.[N+:16]([C:19]1[C:20]([Cl:26])=[N:21][CH:22]=[N:23][C:24]=1Cl)([O-:18])=[O:17]>O1CCCC1.C(OCC)(=O)C>[Cl:26][C:20]1[N:21]=[CH:22][N:23]=[C:24]([NH:1][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=2)[C:19]=1[N+:16]([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 203124,6-Dichloro-5-nitropyrimidineHCID 844322-Chloropyridin-4-amine

Product 1

HCID 22597426HCID 22597426, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Amino-2-chloropyridine (8.0 g, 62.2 mmol) and triethylamine (8.7 mL) were added. successively to a suspension of 5-nitro-4,6-dichloropyrimidine (8.0 g, 41.2 mmol) in tetrahydrofuran (160 mL), and the mixture was heated under reflux for 4 hours. After cooling as it was, the reaction solution was diluted with ethyl acetate (160 ml) and washed with 160 ml water and brine, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue were suspended in diethyl ether, and the resulting solid was collected by filtration and air-dried, to give the title compound (2.2 g, 19%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling as it
  4. washwashed with 160 ml water and brine
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. filtrationthe resulting solid was collected by filtration
  8. customair-dried

Sources & evidence

ORD record
ord-b20c33ebc8e9423d8180eb4acd9dc76b
Source dataset
uspto-grants-2005_01
Patent number
US06841549B1

Reaction notes

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