Sodium hydride → HCID 178463588, compound

HRID 634451Notes

Reaction equation

HRID 634451 reaction equation
C([N:20]1[CH:28]=[N:27][C:26]2[C:21]1=[N:22][CH:23]=[N:24][C:25]=2[NH:29]C(=O)OC(C)(C)C)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Br[CH:38]([C:40]1[O:41][C:42](=[O:56])[C:43]2[C:48]([C:49]=1[C:50]1[CH2:51][CH2:52][O:53][CH2:54][CH:55]=1)=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH3:39].[H-].[Na+]>CN(C=O)C>[N:24]1[C:25]([NH:29][CH:38]([C:40]2[O:41][C:42](=[O:56])[C:43]3[C:48]([C:49]=2[C:50]2[CH2:51][CH2:52][O:53][CH2:54][CH:55]=2)=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH3:39])=[C:26]2[C:21]([NH:20][CH:28]=[N:27]2)=[N:22][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 70974658tert-butyl N-(9-tritylpurin-6-yl)carbamateHCID 1181312613-(1-bromoethyl)-4-(3,6-dihydro-2H-pyran-4-yl)-1H-isochromen-1-one

Product 1

HCID 178463588HCID 178463588, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was made in a similar way as that of the compound of example 21, from tert-butyl 9-trityl-9H-purin-6-ylcarbamate (214 mg, 0.449 mmol) and 3-(1-bromoethyl)-4-(3,6-dihydro-2H-pyran-4-yl)-1H-isochromen-1-one (intermediate C19, 94 mg, 0.280 mmol) and 50% dispersion in mineral oil NaH (18 mg, 0.34 mmol) in DMF. This was purified via reverse phase chromatography with a Biotage C18 SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%). Fractions containing the required product were collected, 1 M HClaqueous (5 ml) was added and concentrated under reduced pressure to give the title compound (6.3 mg, 5.8%) as colourless solid.

Workup

  1. customThis was purified via reverse phase chromatography with a Biotage C18 SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%)
  2. additionFractions containing the required product
  3. customwere collected
  4. addition1 M HClaqueous (5 ml) was added
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-788cea912d934b03b29c8ee52bc8b543
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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