Benzyl Bromide → HCID 58126934, compound

HRID 1971816Notes

Reaction equation

HRID 1971816 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[N:15]([CH2:16][C:17](=[O:24])[N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:14]=[CH:13][N:8]2[C:9](=[O:12])[C:10]=1[OH:11])=[O:4].C([O-])([O-])=O.[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[N:15]([CH2:16][C:17](=[O:24])[N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:14]=[CH:13][N:8]2[C:9](=[O:12])[C:10]=1[O:11][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 581269886-Hydroxy-5-oxo-1-(2-oxo-2-piperidin-1-yl-ethyl)-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester

Product 1

HCID 58126934HCID 58126934, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The crude product of example 2 was dissolved in DMF (50 ml) and then K2CO3 (3.3 g, 0.024 mol) was added. After stirring at room temperature for about 0.5 hours, benzyl bromide (4.0 g, 0.0234 mol) was added drop-wise. Then the mixture was heated at 80° C. for another 5 hours. After cooling to room temperature, the solids were filtered off and washed with ethyl acetate. The filtrate was diluted with EA, washed with water and then brine, dried and concentrated. The residue was purified by column chromatography (CH2Cl2/MeOH=50/1) to give the titled compound (2.0 g, 2-step yield 49.3%).

Workup

  1. temperatureThen the mixture was heated at 80° C. for another 5 hours
  2. temperatureAfter cooling to room temperature
  3. filtrationthe solids were filtered off
  4. washwashed with ethyl acetate
  5. additionThe filtrate was diluted with EA
  6. washwashed with water
  7. dry with materialbrine, dried
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (CH2Cl2/MeOH=50/1)

Sources & evidence

ORD record
ord-f4a304265470460eb1494a1cdf2f4e59
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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