Hydrochloric Acid → 6H-Purin-6-one, 2-amino-1,7-dihydro-7-(2-propen-1-yl)-

HRID 2200630Notes

Reaction equation

HRID 2200630 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:20])[C:5]2[N:6]=[CH:7][N:8]([C@H]3[C@@H](O)[C@@H](O)[C@H](CO)O3)[C:9]=2[N:10]=1.[CH2:21](Br)[CH:22]=[CH2:23].Cl.[OH-].[Na+]>CS(C)=O.O>[CH2:23]([N:6]1[C:5]2[C:4](=[O:20])[NH:3][C:2]([NH2:1])=[N:10][C:9]=2[N:8]=[CH:7]1)[CH:22]=[CH2:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 1366141282-amino-9-((2R,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one

Product 1

HCID 1354353176H-Purin-6-one, 2-amino-1,7-dihydro-7-(2-propen-1-yl)-Yield 59.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2-amino-9-((2R,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one (50 g, 176.7 mmol) in DMSO (150 mL) was added allyl bromide (36 mL, 420 mmol), the mixture was stirred at room temperature overnight under nitrogen atmosphere. The reaction was chilled to 0° C. concentrated HCl (100 mL) was added and the reaction was stirred at 70° C. for 4 h. The reaction was cooled to room temperature, poured into water (800 mL), and neutralized with 6N sodium hydroxide to pH 7-8. The solids that formed were collected and the filter cake was washed with water and ethanol, then dried under vacuum to give 7-allyl-2-amino-1H-purin-6(7H)-one (20 g, 59.2% yield) as yellow solid. LCMS retention time 0.330 min; LCMS MH+ 192.

Workup

  1. additionwas added
  2. stirringthe reaction was stirred at 70° C. for 4 h
  3. temperatureThe reaction was cooled to room temperature
  4. customThe solids that formed
  5. customwere collected
  6. washthe filter cake was washed with water and ethanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-3fff53e00e6b405699a8f48a9bf63e0e
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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