p-Toluenesulfonic acid → HCID 136409750, compound

HRID 1439718Notes

Reaction equation

HRID 1439718 reaction equation
C(O)(=O)C.C(O)(=O)C.[NH:9]1[C:18](=[O:19])[C:17]2[NH:16][CH:15]=[N:14][C:13]=2[N:12]=[C:10]1[NH2:11].C(OC[O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][C:32](=O)C1C=CC=CC=1)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[OH:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][N:14]1[CH:15]=[N:16][C:17]2[C:18](=[O:19])[NH:9][C:10]([NH2:11])=[N:12][C:13]1=2

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 21396260HCID 21396260, compoundHCID 136409751HCID 136409751, compound

Product 1

HCID 136409750HCID 136409750, compoundYield 6.2%

Conditions

Temperature
120 °C

Procedure

A mixture of guanine diacetate (1.31 g), 2-(2-benzoyloxyethoxy)ethoxymethyl acetate (2.37 g), p-toluenesulfonic acid (32 mg) and mineral oil (5.2 g) was heated at 120° C. with stirring for 18 hours. The reaction mixture was cooled and the mineral oil decanted off. The residue was triturated with benzene and the benzene decanted off. To the residue was added 40% aqueous methylamine (10 ml), and the mixture was heated in a steam bath for 30 minutes. The water and methylamine were removed under reduced pressure and the residue extracted with hot ethanol. The ethanol-insoluble material was dissolved in boiling methanol, filtered, concentrated to 125 ml and cooled to room temperature, precipitating an impure product (166 mg) which was unmoved by filtration. The filtrate was chilled and 9-[2-(2-hydroxyethoxy)ethoxymethyl]guanine (80 mg, m.p. 184°-187° C.) was obtained.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe mineral oil decanted off
  3. customThe residue was triturated with benzene
  4. customthe benzene decanted off
  5. additionTo the residue was added 40% aqueous methylamine (10 ml)
  6. temperaturethe mixture was heated in a steam bath for 30 minutes
  7. customThe water and methylamine were removed under reduced pressure
  8. extractionthe residue extracted with hot ethanol
  9. dissolutionThe ethanol-insoluble material was dissolved
  10. filtrationfiltered
  11. concentrationconcentrated to 125 ml
  12. temperaturecooled to room temperature
  13. customprecipitating an impure product (166 mg) which
  14. filtrationwas unmoved by filtration
  15. temperatureThe filtrate was chilled

Sources & evidence

ORD record
ord-82cf2a284ef84468a449c053a237497b
Source dataset
uspto-grants-1977_11
Patent number
US04060616

Reaction notes

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