Water → N-[5-(5-Bromo-2-chloro-pyrimidin-4-ylamino)-pentyl]-3-nitro-benzenesulfonamide

HRID 970414Notes

Reaction equation

HRID 970414 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1)(=[O:19])=[O:18].C(N(CC)CC)C.O>C(#N)C>[Br:1][C:2]1[C:3]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)(=[O:18])=[O:19])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 12147933N-(5-Amino-pentyl)-3-nitro-benzenesulfonamide

Product 1

HCID 12147934N-[5-(5-Bromo-2-chloro-pyrimidin-4-ylamino)-pentyl]-3-nitro-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 1.2 g (5.3 mmol) of 5-bromo-2,4-dichloro-pyrimidine in 30 ml of acetonitrile is added to a solution of 1.5 g (5.2 mmol) of N-(5-amino-pentyl)-3-nitro-benzenesulfonamide in 50 ml of acetonitrile. The reaction mixture is mixed with 1.0 ml (7.2 mmol) of triethylamine and stirred for 17 hours at room temperature. After water (50 ml) is added, it is extracted (2×) with ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (hexane/ethyl acetate 2:1, Flashmaster II). 1.5 g (3.1 mmol, corresponding to 60% of theory) of the product is obtained.

Workup

  1. extractionit is extracted (2×) with ethyl acetate
  2. dry with materialThe combined organic phases are dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe remaining residue is purified by chromatography (hexane/ethyl acetate 2:1, Flashmaster II)
  6. custom1.5 g (3.1 mmol, corresponding to 60% of theory) of the product is obtained

Sources & evidence

ORD record
ord-6ea098fa618e457e8aae34f00759fef7
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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