Allyl bromide → HCID 18187648, compound

HRID 1357904Notes

Reaction equation

HRID 1357904 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[CH2:31](Br)[CH:32]=[CH2:33].[Cl-].[NH4+]>C1COCC1.C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]([CH:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]1)[CH2:33][CH:32]=[CH2:31]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 2763949tert-butyl 4-(pyrimidin-2-ylamino)piperidine-1-carboxylate

Product 1

HCID 18187648HCID 18187648, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(N-(pyrimidin-2-yl)amino)-1-t-butoxycarbonylpiperidine from Step B (528 mg, 1.9 mmol) in dry THF (5 mL) was cooled to −78° C. and a solution of sodium hexamethyldisilazide (2.8 mL, 1.0 M in THF, 2.8 mmol) was added via syringe. The mixture was stirred cold for 20 min then allyl bromide (0.23 mL, 2.7 mmol) was added. The mixture was then warmed to rt and stirred for 1.5 h at which time TLC showed very little starting material. The solution was poured into sat'd ammonium chloride and methylene chloride. The layers were separated and the organic phase was dried over sodium sulfate and concentrated. FC (25 g silica, 4/1 hexanes/ethyl acetate) afforded the title compound (367 mg).

Workup

  1. stirringstirred for 1.5 h at which time TLC
  2. customThe layers were separated
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7af16b625241427ea4fbbb4d282bfb13
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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