Water → HCID 58891333, compound

HRID 970448Notes

Reaction equation

HRID 970448 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.[CH2:17]([O:24][C:25](=[O:33])[NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH2:32])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(#N)C>[CH2:17]([O:24][C:25](=[O:33])[NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 2794259N-Carbobenzoxy-1,5-diaminopentane hydrochloride

Product 1

HCID 58891333HCID 58891333, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 860 mg (3.8 mmol) of 5-bromo-2,4-dichloro-pyrimidine and 1.2 ml (8.5 mmol) of triethylamine in 6 ml of acetonitrile is mixed at 0° C. with 1.0 g (3.7 mmol) of (5-amino-pentyl)-carbamic acid-benzyl ester. The reaction mixture is slowly heated to room temperature while being stirred by removal of the ice bath. After 60 hours, it is mixed with water and then extracted with ethyl acetate (2×). The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The residue that is formed is purified by chromatography (hexane/ethyl acetate 1:1). 1.2 g (2.8 mmol, corresponding to 77% of theory) of the product is obtained.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. dry with materialThe combined organic phases are dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe residue that is formed
  6. customis purified by chromatography (hexane/ethyl acetate 1:1)
  7. custom1.2 g (2.8 mmol, corresponding to 77% of theory) of the product is obtained

Sources & evidence

ORD record
ord-26e3a7115ee54c9ba984234a24db5642
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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