Triethylamine → HCID 59020397, compound

HRID 970418Notes

Reaction equation

HRID 970418 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[C:10]([NH:17][CH2:18][CH2:19][CH2:20][NH2:21])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[C:13]([O:12][C:10](=[O:11])[NH:17][CH2:18][CH2:19][CH2:20][NH:21][C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 59020397HCID 59020397, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6.1 g (26.6 mmol) of 5-bromo-2,4-dichloro-pyrimidine in 100 ml of acetonitrile is mixed successively with 5.0 g (28.7 mmol) of N-boc-1,3-diaminopropane and 4.5 ml (32.4 mmol) of triethylamine and stirred for 3.5 hours at room temperature. The batch is diluted with 200 ml of ethyl acetate. It is washed with saturated NaCl solution, citric acid (10%), saturated NaHCO3 solution as well as saturated NaCl solution. The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. 9.7 g (26.6 mmol, corresponding to 100% of theory) of the product is obtained.

Workup

  1. washIt is washed with saturated NaCl solution, citric acid (10%), saturated NaHCO3 solution as well as saturated NaCl solution
  2. dry with materialThe combined organic phases are dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. custom9.7 g (26.6 mmol, corresponding to 100% of theory) of the product is obtained

Sources & evidence

ORD record
ord-512e97e0cfa140f8a15a9954a3286810
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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