Hexahydro-1,4-diazepine → 1-(5-bromopyrimidin-2-yl)-1,4-diazepane

HRID 1446099Notes

Reaction equation

HRID 1446099 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH:9]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>CC#N>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:9]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 27610401-(5-bromopyrimidin-2-yl)-1,4-diazepaneYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-Bromo-2-chloro-pyrimidine (1.0 g, 5.1 mmol), [1,4]Diazepane (1.0 g, 10.2 mmol) in CH3CN (5.0 mL) was stirred at 50° C. for 3 hrs. Filter of the solid and the solution was washed with brine, and concentrated in vacuo to give the title product (1.1 g, 85%) as a brown solid. ESI MS m/z 258 (M+H+); 1H NMR (400 MHz, CDCl3) δ 8.22 (s, 2H), 3.77 (m, 4H), 2.97 (q, J=10 Hz, 2H), 2.81 (q, J=15 Hz, 2H), 2.02 (s, 1H) 1.83 (qt, J=15 Hz, 2H).

Workup

  1. filtrationFilter of the solid
  2. washthe solution was washed with brine
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b43e468d50f2448d947416e17cfa36da
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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