Chlorosuccinimide → HCID 90403083, compound

HRID 2200626Notes

Reaction equation

HRID 2200626 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:12][CH:11]([N:13]2[C:21](=[O:22])[C:20]3[N:19]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=4)[CH:18]=[N:17][C:16]=3[N:15]([CH3:31])[C:14]2=[O:32])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Cl:40])C(=O)C1>CN(C=O)C>[CH2:1]([O:8][CH:9]1[CH2:10][CH:11]([N:13]2[C:21](=[O:22])[C:20]3[N:19]([CH2:23][C:24]4[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=4)[C:18]([Cl:40])=[N:17][C:16]=3[N:15]([CH3:31])[C:14]2=[O:32])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 90402523HCID 90402523, compound

Product 1

HCID 90403083HCID 90403083, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-(benzyloxy)cyclobutyl)-7-(4-chlorobenzyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (220 mg, 0.49 mmol) in DMF (3 mL) was added NCS (71.7 mg, 0.54 mmol) in portions at 0° C. The reaction was stirred at room temperature for 4 h. The reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried and concentrated to give a crude product, which was purified by silica gel chromatography eluting with DCM/methanol (60:1) to give 1-(3-(benzyloxy)cyclobutyl)-8-chloro-7-(4-chlorobenzyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (170 mg, 71.8% yield) as yellow solid. LCMS retention time 2.079 min; LCMS MH+ 485.

Workup

  1. customThe reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. washThe organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customto give a crude product, which
  6. customwas purified by silica gel chromatography
  7. washeluting with DCM/methanol (60:1)

Sources & evidence

ORD record
ord-7fef6523f6b04927a0cb8315258da851
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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