Propyl mercaptan → HCID 90403387, compound

HRID 2200711Notes

Reaction equation

HRID 2200711 reaction equation
Br[C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]2[C:8](=[O:19])[N:7]([CH2:20][CH2:21][CH:22]([OH:24])[CH3:23])[C:6](=[O:25])[N:5]([CH3:26])[C:4]=2[N:3]=1.[CH2:27]([SH:30])[CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:10]2[C:9]3[C:8](=[O:19])[N:7]([CH2:20][CH2:21][CH:22]([OH:24])[CH3:23])[C:6](=[O:25])[N:5]([CH3:26])[C:4]=3[N:3]=[C:2]2[S:30][CH2:27][CH2:28][CH3:29])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 11430Potassium CarbonateHCID 90402996HCID 90402996, compound

Product 1

HCID 90403387HCID 90403387, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 8-bromo-7-(4-chlorobenzyl)-1-(3-hydroxybutyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (100 mg, 0.23 mmol, example 97, step 1) in DMF (5 mL) was added propane-1-thiol (20.7 mg, 0.27 mmol) followed by potassium carbonate (93.9 mg, 0.68 mmol). The reaction was stirred at 60° C. for 3 h. The reaction was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product (80 mg, 80.9% yield) as yellow oil. LCMS MH+ 437.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-06eee480205f46f4856098eb8b9a2601
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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