Triethylamine → HCID 17986368, compound

HRID 970430Notes

Reaction equation

HRID 970430 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[N+:17]([C:20]1[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=1)[O:23][CH2:24][CH2:25][CH2:26][CH2:27][NH2:28])([O-:19])=[O:18]>C(#N)C.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([NH:28][CH2:27][CH2:26][CH2:25][CH2:24][O:23][C:22]2[CH:29]=[CH:30][CH:31]=[C:20]([N+:17]([O-:19])=[O:18])[CH:21]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 17986370HCID 17986370, compound

Product 1

HCID 17986368HCID 17986368, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.28 g (10 mmol) of 5-bromo-2,4-dichloro-pyrimidine and 1.4 ml of triethylamine (10 mmol) in 32 ml of acetonitrile is mixed at 4° C. while being stirred with a solution of 2.1 g (10 mmol) of 4-(3-nitro-phenoxy)-butylamine in 5 ml of acetonitrile. After 12 hours, it is diluted with ethyl acetate and filtered. The filtrate is concentrated by evaporation in a rotary evaporator, and the remaining residue is purified by chromatography (hexane/ethyl acetate 1:1, Flashmaster II). 2.7 g (7 mmol, corresponding to 70% of theory) of the product is obtained.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated by evaporation in a rotary evaporator
  3. customthe remaining residue is purified by chromatography (hexane/ethyl acetate 1:1, Flashmaster II)
  4. custom2.7 g (7 mmol, corresponding to 70% of theory) of the product is obtained

Sources & evidence

ORD record
ord-3b288ef18889436c97a93d470785bf1c
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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