Bromocyclopentane → HCID 9995649, compound

HRID 2056247Notes

Reaction equation

HRID 2056247 reaction equation
[CH2:1]([C:5]1[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]=[C:10]2[C:6]=1[NH:7][CH:8]=[N:9]2)[CH2:2][CH2:3][CH3:4].Br[CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([C:5]1[N:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 69079899HCID 69079899, compound

Product 1

HCID 9995649HCID 9995649, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(1-butyl)-2-trifluoromethylpurine (35 mg, 0.14 mmol), bromocyclopentane (89 mg, 0.60 mmol), potassium carbonate (83 mg, 0.6 mmol) and N,N-dimethylformamide (3 ml) was heated to 100° C. After 8 hours, the reaction mixture was cooled to 40° C. and concentrated under vacuum. The residue was treated with 15 ml of ethyl acetate and washed with 5% sodium bicarbonate (2×15 mL). The organic layer was concentrated and purified by chromatography (20% ethyl acetate in hexane) to give 6-(1-butyl)-9-cyclopentyl-2-trifluoromethylpurine (26.6 mg, 60% yield).

Workup

  1. temperaturethe reaction mixture was cooled to 40° C.
  2. concentrationconcentrated under vacuum
  3. additionThe residue was treated with 15 ml of ethyl acetate
  4. washwashed with 5% sodium bicarbonate (2×15 mL)
  5. concentrationThe organic layer was concentrated
  6. custompurified by chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-32b6f56500c9413e85c46589722acc3a
Source dataset
uspto-grants-2008_02
Patent number
US07335654B2

Reaction notes

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