Cyclobutylamine → HCID 178478379, compound

HRID 2182750Notes

Reaction equation

HRID 2182750 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4](Cl)[N:3]=1.C(N(CC)C(C)C)(C)C.[CH:21]1([NH2:25])[CH2:24][CH2:23][CH2:22]1>C(O)CCC>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([NH:25][CH:21]2[CH2:24][CH2:23][CH2:22]2)[N:3]=1

Participants

5

Reactant 3

HCID 75645CyclobutylamineHCID 81531DiisopropylethylamineHCID 1784188752,6-dichloro-1H-purine

Product 1

HCID 178478379HCID 178478379, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Conditions

Temperature
75 °C

Procedure

A 12 L, 4-neck, round-bottomed flask fitted with a mechanical stirrer, digital thermometer, heating and cooling capabilities, condenser, addition funnel, and nitrogen inlet and outlet, was flushed with nitrogen and charged with 492.9 g (2.61 moles) of 2,6-dichloro-9H-purine, 497.7 mL (2.87 moles) of N,N-diisopropylethylamine, and 3.65 L of anhydrous 1-butanol. The mixture was stirred and heated to 75° C. and 244.9 mL (2.87 moles) of cyclobutylamine in 1.25 L of anhydrous 1-butanol, was added during about 1 hour at a temperature of 75° C.-77° C. The reaction temperature and stirring was maintained for 4.5 hours. The mixture was cooled to 5° C. over a period of 1 hour. The product was filtered and the filter cake was washed three times with a total of 0.9 L of 1-butanol. The filter cake was collected and dried at 75° C./20 mm Hg for 24 hours to give 506.6 g of light yellow crystalline solid. Theoretical yield was 583.3 g. Actual yield was 86.9%.

Workup

  1. customA 12 L, 4-neck, round-bottomed flask fitted with a mechanical stirrer
  2. temperaturedigital thermometer, heating
  3. temperaturecooling
  4. additioncapabilities, condenser, addition funnel, and nitrogen inlet and outlet
  5. customwas flushed with nitrogen
  6. stirringThe reaction temperature and stirring
  7. temperaturewas maintained for 4.5 hours
  8. temperatureThe mixture was cooled to 5° C. over a period of 1 hour
  9. filtrationThe product was filtered
  10. washthe filter cake was washed three times with a total of 0.9 L of 1-butanol
  11. customThe filter cake was collected
  12. customdried at 75° C./20 mm Hg for 24 hours

Sources & evidence

ORD record
ord-7e7127ee23f34affa3231ad10eaec94d
Source dataset
uspto-grants-2005_05
Patent number
US06897307B2

Reaction notes

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