Ethyl Bromide → HCID 13784146, compound

HRID 569999Notes

Reaction equation

HRID 569999 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[CH:16][C:17]3[NH:18][C:19](=[O:25])[CH2:20][CH2:21][CH2:22][C:23]=3[N:24]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:28](Br)[CH3:29]>C1COCC1>[CH2:28]([N:18]1[C:19](=[O:25])[CH2:20][CH2:21][CH2:22][C:23]2[N:24]=[C:14]([N:11]3[CH2:10][CH2:9][N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:13][CH2:12]3)[N:15]=[CH:16][C:17]1=2)[CH3:29]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 13784145HCID 13784145, compound

Product 1

HCID 13784146HCID 13784146, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Added to 30 ml of THF were 0.65 g (1.84 mmol, Referential Example 51) of 2-(4-benzylpiperazino)-6-oxo-6,7,8,9-tetrahydro(5H)pyrimido[5,4-b]azepine and 0.15 g (3.75 mmol) of 60% NaH. The resultant mixture was stirred at 20° C. for 30 minutes. Thereafter, 3 g (27.8 mmol) of ethyl bromide was added and the reaction mixture was heated to 60° C. at which the reaction was conducted for 5 hours. After completion of the reaction, the solvent was distilled off and the residue was purified by silica gel column chromatography to obtain 0.65 g of a colorless oil (yield: 92%).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1d7711ee40d045a597ef5c7fabbd7579
Source dataset
uspto-grants-1988_03
Patent number
US04734418

Reaction notes

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