Sodium hydride → HCID 178456863, compound

HRID 634452Notes

Reaction equation

HRID 634452 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:41]1[O:42][C:43](=[O:57])[C:44]2[C:49]([C:50]=1[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:39][CH3:40].[H-].[Na+]>CN(C=O)C>[N:24]1[C:25]([NH:29][CH:38]([C:41]2[O:42][C:43](=[O:57])[C:44]3[C:49]([C:50]=2[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:39][CH3:40])=[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 1181311823-(1-Bromopropyl)-4-phenyl-1H-isochromen-1-one

Product 1

HCID 178456863HCID 178456863, compoundYield 2.4%

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 (167 mg, 0.350 mmol), 3-(1-bromopropyl)-4-phenyl-1H-isochromen-1-one (intermediate C20, 100 mg, 0.291 mmol) and 50% dispersion in mineral oil NaH (21 mg, 0.870 mmol) in DMF at 55° C. The crude was purified via reverse phase chromatography with a column stacking of two Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%) and further purified by Preparative HPLC (method 1) to give the title compound (2.8 mg, 2.4%) as a colourless solid.

Workup

  1. customat 55° C
  2. customThe crude was purified via reverse phase chromatography with a column stacking of two Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%)
  3. customPhase B ACN 95%, water 5%, formic acid 0.1%) and further purified by Preparative HPLC (method 1)

Sources & evidence

ORD record
ord-5947bb1296704c6686fc16fada640522
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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