Borane → {4-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-butyl}methyl-carbamic acid tert-butyl ester

HRID 219701Notes

Reaction equation

HRID 219701 reaction equation
[C:1]([O:5][C:6](=[O:34])[N:7]([CH2:9][CH2:10][CH2:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[C:24]([CH:26]3[CH2:29][CH2:28][CH2:27]3)[N:23]=[C:22]([C:30]([CH3:33])([CH3:32])[CH3:31])[N:21]=2)[CH2:16][CH2:15]1)=O)[CH3:8])([CH3:4])([CH3:3])[CH3:2].B>O1CCCC1>[C:1]([O:5][C:6](=[O:34])[N:7]([CH2:9][CH2:10][CH2:11][CH2:12][N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[C:24]([CH:26]3[CH2:27][CH2:28][CH2:29]3)[N:23]=[C:22]([C:30]([CH3:33])([CH3:32])[CH3:31])[N:21]=2)[CH2:16][CH2:15]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6331BoraneHCID 69026620{4-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-4-oxo-butyl}-methyl-carbamic acid tert-butyl ester

Product 1

HCID 69028122{4-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-butyl}methyl-carbamic acid tert-butyl esterYield 64.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

13.1 g of {4-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-4-oxo-butyl}-methyl-carbamic acid tert-butyl ester (27.66 mmol) were dissolved in 250 ml of tetrahydrofuran. 44.9 g of borane in tetrahydrofuran (522.44 mmol) were added dropwise within 25 min. and then the reaction mixture was heated to reflux for 1.5 h. The reaction mixture was poured onto water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated to dryness. The crude product was purified by chromatography on silica gel using dichloromethane-methanol (0-5%) as eluent. Fractions containing the product were combined and the solvent evaporated to yield 8.2 g of the title compound.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1.5 h
  3. additionThe reaction mixture was poured onto water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude product was purified by chromatography on silica gel
  9. additionFractions containing the product
  10. customthe solvent evaporated

Sources & evidence

ORD record
ord-c0a4a2fc5e794c1cb50e820c7de0d35c
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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