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

HRID 1274690Notes

Reaction equation

HRID 1274690 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-c745d2986d5f4da69bdb545324c69d84
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

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