Potassium Carbonate → HCID 67367823, compound

HRID 1910948Notes

Reaction equation

HRID 1910948 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[NH:20][CH2:19][CH2:18][N:9]2[C:10](=[O:17])[C:11]2[N:12]([CH:14]=[CH:15][CH:16]=2)[CH2:13]3)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>CN(C=O)C.[NH4+].[Cl-]>[Si:31]([O:30][CH2:29][CH2:28][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[NH:20][CH2:19][CH2:18][N:9]2[C:10](=[O:17])[C:11]2[N:12]([CH:14]=[CH:15][CH:16]=2)[CH2:13]3)=[CH:4][CH:3]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 67370128HCID 67370128, compound

Product 1

HCID 67367823HCID 67367823, compoundYield 105.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 10a-(4-hydroxyphenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (50 mg, 0.19 mmol) and potassium carbonate (77 mg, 0.56 mmol) in DMF (1 mL) was added (2-bromoethoxy)-tert-butyldimethylsilane (120 μL, 0.56 mmol). The mixture was heated at 100° C. The outcome of the reaction was monitored by LCMS. After completion (45 minutes) the mixture was diluted with a saturated aqueous solution of NH4Cl (6 mL) and extracted with ethyl acetate (3×2.5 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to yield a pale yellow solid that was purified by flash chromatography (Biotage SP4, 12 g silica cartridge, gradient 0-10% MeOH in CH2Cl2) to give 10a-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)phenyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (86 mg, quantitative yield). ESI-MI m/z [M+H]+ 428.2.

Workup

  1. extractionextracted with ethyl acetate (3×2.5 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto yield a pale yellow solid
  6. customthat was purified by flash chromatography (Biotage SP4, 12 g silica cartridge, gradient 0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-cfaf906f0a28428ba57a3adeedce4c3f
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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