Cyclopentanol → HCID 90111371, compound

HRID 1508946Notes

Reaction equation

HRID 1508946 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Cl:9][C:10]1[C:11]2[CH2:22][CH2:21][CH2:20][C:12]=2[N:13]=[C:14](S(C)(=O)=O)[N:15]=1>C1COCC1.O>[Cl:9][C:10]1[C:11]2[CH2:22][CH2:21][CH2:20][C:12]=2[N:13]=[C:14]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[N:15]=1

Participants

6

Reactant 3

HCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 21927804HCID 21927804, compound

Product 1

HCID 90111371HCID 90111371, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of cyclopentanol (0.287 g, 3.33 mmol) in THF (5 mL) was added sodium hydride (0.016 g, 0.67 mmol) and the mixture stirred at rt under a nitrogen atmosphere for 30 min. Then, the mixture was added treated with a solution of 4-chloro-2-(methylsulfonyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (0.155 g, 0.67 mmol) dropwise in THF (2 mL) and the resulting mixture stirred at rt for 2 h. After this time, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/dichloromethane) to afford the title compound (0:080 g, 52%). MW=238.71. 1H NMR (CD3OD, 300 MHz) δ 5.64-5.40 (m, 1H), 2.90 (t, J=7.6 Hz, 2H), 2.78 (t, J=7.6 Hz, 2H), 2.21-2.08 (m, 2H), 1.90-1.71 (m, 4H), 1.71-1.59 (m, 2H), 1.38-1.18 (m, 2H); APCI MS m/z 239 [M+H]+.

Workup

  1. additionThen, the mixture was added
  2. stirringthe resulting mixture stirred at rt for 2 h
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by column chromatography (silica, hexanes/dichloromethane)

Sources & evidence

ORD record
ord-8af25d87f3ea48fab1b1eabf8b89c87d
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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