Water → tert-Butyl (1-oxo-4-phenyl-1H-isochromen-3-yl)methyl(9-trityl-9H-purin-6-yl)carbamate

HRID 634455Notes

Reaction equation

HRID 634455 reaction equation
[C:1]([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:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:40][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.O>CN(C=O)C>[O:57]=[C:43]1[C:44]2[C:49](=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:50]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[C:41]([CH2:40][N:29]([C:25]2[N:24]=[CH:23][N:22]=[C:21]3[C:26]=2[N:27]=[CH:28][N:20]3[C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])[O:42]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 70974658tert-butyl N-(9-tritylpurin-6-yl)carbamateHCID 1181311893-(Bromomethyl)-4-phenyl-1H-isochromen-1-one2×

Product 1

HCID 118150091tert-Butyl (1-oxo-4-phenyl-1H-isochromen-3-yl)methyl(9-trityl-9H-purin-6-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

tert-Butyl 9-trityl-9H-purin-6-ylcarbamate (63.6 mg, 0.133 mmol) in DMF (0.1 ml) was added to a suspension of 50% dispersion in mineral oil NaH (5.33 mg, 0.133 mmol) in DMF (0.1 ml) at 0° C. 3-(bromomethyl)-4-phenyl-1H-isochromen-1-one (intermediate C1, 35 mg, 0.111 mmol) in DMF (0.2 ml) was added and the resulting mixture was allowed to warm to RT. The reaction mixture was then poured into water and extracted with EtOAc. The collected organic phases were dried and concentrated under reduced pressure and the resulting crude (80 mg) was used in the next step without any further purification and characterization.

Workup

  1. extractionextracted with EtOAc
  2. customThe collected organic phases were dried
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting crude (80 mg) was used in the next step without any further purification and characterization

Sources & evidence

ORD record
ord-d27f4207b4b54cc99b766ddbb4242376
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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