Tert-Butylamine → 4-(t-Butylamino)-2-chloro-5-fluoropyrimidine

HRID 610201Notes

Reaction equation

HRID 610201 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[C:10]([NH2:14])([CH3:13])([CH3:12])[CH3:11]>C(#N)C>[C:10]([NH:14][C:6]1[C:5]([F:9])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 221212264-(t-Butylamino)-2-chloro-5-fluoropyrimidineYield 52.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To 20 ml of acetonitrile were added 6.4 g of 2,4-dichloro-5-fluoropyrimidine and 7.0 g of t-butylamine, then the mixture was stirred at 50° C. for 20 minutes. The solution was concentrated under reduced pressure, and separated by adding 40 ml of distilled water and 70 ml of chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The precipitated pale yellow crystals were dispersed in diisopropylether and collected by filtration to obtain 4.1 g of the title compound.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customseparated
  3. additionby adding 40 ml of distilled water and 70 ml of chloroform
  4. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe precipitated pale yellow crystals were dispersed in diisopropylether
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-2f60c291cca54312a4d99abf544b4a9b
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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