Acetic Anhydride → HCID 136072598, compound

HRID 622670Notes

Reaction equation

HRID 622670 reaction equation
Br[C:2]1[N:3]([CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[C:4]2[N:5]=[C:6]([NH2:12])[NH:7][C:8](=[O:11])[C:9]=2[N:10]=1.C(OC(=O)C)(=[O:21])C.C([O-])(=O)C.[Na+]>C(O)(=O)C>[NH2:12][C:6]1[NH:7][C:8](=[O:11])[C:9]2[NH:10][C:2](=[O:21])[N:3]([CH2:13][C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)[C:4]=2[N:5]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 136096006HCID 136096006, compound

Product 1

HCID 136072598HCID 136072598, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 8-bromo-9-[(2-thienyl)methyl]guanine (see Example 5) (3.12 g; 9.56 mmol), acetic anhydride (75 ml), glacial acetic acid (75 ml) and anhydrous sodium acetate (14.9 g; 0.1816 mol) was heated to reflux for 20 hours. The dark solution which formed was then evaporated to dryness under reduced pressure. The residue was dissolved in aqueous methylamine (150 ml), stirred at room temperature for 48 hours and then heated to reflux for 2.5 hours. The methylamine was distilled off under reduced pressure and the residue was recrystallized from boiling methanol-water mixture to give 1.23 g of the analytical product, mp >300° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. customThe dark solution which formed
  4. customwas then evaporated to dryness under reduced pressure
  5. dissolutionThe residue was dissolved in aqueous methylamine (150 ml)
  6. temperatureheated
  7. temperatureto reflux for 2.5 hours
  8. distillationThe methylamine was distilled off under reduced pressure
  9. customthe residue was recrystallized

Sources & evidence

ORD record
ord-83bb35fb47be4a39a4c7823437b9f507
Source dataset
uspto-grants-1988_09
Patent number
US04772606

Reaction notes

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