Tert-Butylamine → HCID 22326752, compound

HRID 970424

Reaction equation

HRID 970424 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9](Cl)=[O:10])=[CH:4][N:3]=1.[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>C1COCC1>[C:12]([NH:16][C:9]([C:5]1[C:6]([Cl:8])=[N:7][C:2]([Cl:1])=[N:3][CH:4]=1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 137841122,4-Dichloropyrimidine-5-carbonyl chloride

Product 1

HCID 22326752HCID 22326752, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 24.85 g (117.5 mmol) of 2,4-dichloro-pyrimidine-5-carbonyl chloride in 125 ml of THF is cooled to −15° C. It is slowly mixed with a solution of 13.2 ml (124.5 mmol) of tert-buylamine and 17.4 ml (125.7 mmol) of triethylamine in 50 ml of THF, so that the temperature of the reaction mixture remains less than −10° C. It is stirred for another 2 hours at −10° C., then the cooling bath is removed, and the reaction mixture is heated to room temperature while being stirred. After 1 hour, the precipitate that is formed is filtered off, and the filtrate is completely concentrated by evaporation. The residue that is obtained is purified by chromatography (hexane/ethyl acetate 4:1). 14.01 g (56.6 mmol, corresponding to 50% of theory) of the product is obtained.

Workup

  1. customremains less than −10° C
  2. customthe cooling bath is removed
  3. temperaturethe reaction mixture is heated to room temperature
  4. stirringwhile being stirred
  5. waitAfter 1 hour
  6. customthe precipitate that is formed
  7. filtrationis filtered off
  8. concentrationthe filtrate is completely concentrated by evaporation
  9. customThe residue that is obtained
  10. customis purified by chromatography (hexane/ethyl acetate 4:1)
  11. custom14.01 g (56.6 mmol, corresponding to 50% of theory) of the product is obtained

Sources & evidence

ORD record
ord-c9ce549a9b4a400299e4e4993e01a424
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Linked notes

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