Benzyl Bromide → HCID 67142831, compound

HRID 574252Notes

Reaction equation

HRID 574252 reaction equation
[C:1]([O:5][C:6](=[O:40])[NH:7][C@H:8]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:9][N:10]1[C:15](=[O:16])[C:14]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][C:18]2=[O:23])=[CH:13][N:12]([CH2:24][C:25]2[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=2[F:32])[C:11]1=[O:33])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:47](Br)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C=O)C.ClCCl>[C:1]([O:5][C:6](=[O:40])[NH:7][C@H:8]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:9][N:10]1[C:15](=[O:16])[C:14]([N:17]2[CH2:22][CH2:21][N:20]([CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH2:19][C:18]2=[O:23])=[CH:13][N:12]([CH2:24][C:25]2[C:26]([F:32])=[CH:27][CH:28]=[CH:29][C:30]=2[F:31])[C:11]1=[O:33])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67142834HCID 67142834, compound

Product 1

HCID 67142831HCID 67142831, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of {(R)-2-[3-(2,6-difluoro-benzyl)-2,6-dioxo-5-(2-oxo-piperazin-1-yl)-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (7) (20 mg, 0.036 mmol) in DMF (1 mL) were added potassium carbonate (12 mg, 0.09 mmol) and benzyl bromide (7 mg, 0.040 mmol) in that order, followed by stirring at room temperature for 1 hr. The solution was diluted with dichloromethane and washed with distilled water. The organic layer thus formed was separated and concentrated, and the residue was purified using silica gel chromatography (eluent: dichloromethane/methanol, 30/1) and dried in a vacuum to afford 22 mg of the compound as a white solid (yield 96%). 1H NMR (300 MHz, CDCl3) δ 1.32 (9H, s), 2.86 (2H, t), 3.32 (2H, s), 3.58 (2H, m), 3.73 (2H, s), 4.04 (1H, m), 4.46 (1H, t), 5.05 (3H, m), 5.53 (1H, m), 6.98 (2H, t), 7.24-7.38 (6H, m), 7.56 (2H, m), 7.71 (1H, d), 8.20 (1H, dd), 8.26 (1H, s)

Workup

  1. washwashed with distilled water
  2. customThe organic layer thus formed
  3. customwas separated
  4. concentrationconcentrated
  5. customthe residue was purified
  6. customdried in a vacuum

Sources & evidence

ORD record
ord-b51540a025b14a67ab30ffb83263a2a3
Source dataset
uspto-grants-2015_05
Patent number
US09034850B2

Reaction notes

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