Hydrochloric Acid → 7-allyl-8-chloro-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione

HRID 2200635Notes

Reaction equation

HRID 2200635 reaction equation
[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][CH2:15][CH2:16][O:17][Si](C(C)(C)C)(C)C)[C:9](=[O:25])[N:8]([CH2:26][CH3:27])[C:7]=2[N:6]=[C:5]1[Cl:28])[CH:2]=[CH2:3].Cl>C(O)C>[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][CH2:15][CH2:16][OH:17])[C:9](=[O:25])[N:8]([CH2:26][CH3:27])[C:7]=2[N:6]=[C:5]1[Cl:28])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 904028127-allyl-1-(3-(tert-butyldimethylsilyloxy)propyl)-8-chloro-3-ethyl-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 904025367-allyl-8-chloro-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dioneYield 136.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-allyl-1-(3-(tert-butyldimethylsilyloxy)propyl)-8-chloro-3-ethyl-1H-purine-2,6(3H,7H)-dione (3.8 g, 8.92 mmol) in ethanol (20 mL) was added concentrated HCl (2 mL). The mixture was stirred at room temperature for 0.5 h. The mixture was concentrated and partitioned between ethyl acetate and saturated sodium bicarbonate. The organic phase was washed with brine and dried over sodium sulfate, and concentrated to give 7-allyl-8-chloro-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (3.8 g) as yellow oil, which was used without purification. LCMS retention time 0.999 min; LCMS MH+ 313.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5e38ebdfbc604d8ca3853e686c4f187b
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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