Acetic Anhydride → HCID 13714021, compound

HRID 64628Notes

Reaction equation

HRID 64628 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][S:12][CH2:13][CH2:14][OH:15])=[CH:4][N:3]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>CN(C)C1C=CN=CC=1.CN(C=O)C>[C:16]([O:15][CH2:14][CH2:13][S:12][CH2:11][N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([NH2:1])=[N:3][CH:4]=2)(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 101307502-amino-9-(2-hydroxyethylthiomethyl)-9H-purine

Product 1

HCID 13714021HCID 13714021, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A 100 ml flask equipped with a magnetic stirring bar and a CaCl2 drying tube was charged with 1.0 g (4.4 mM) 2-amino-9-(2-hydroxyethylthiomethyl)-9H-purine, 0.054 g (0.44 mM) 4-dimethylaminopyridine, 0.9 ml (8.8 mM) acetic anhydride, and 200 ml of dry DMF. The solution was stirred for 24 hrs at room temperature and then quenched with 5 ml of MeOH. The solution was evaporated in vacuo (bath temp 40° C.) and the brown oil so obtained chromatographed using the "flash" method. Elution of the column with 1.5% methanol in ethyl acetate provided a yellow oil which crystallized on standing. The light yellow crystals were dissolved in a solution of 2% MeOH in toluene and treated with 0.05 g Darco G-60. The methanol was evaporated from the toluene solution resulting in the precipitation of light yellow crystals. The product was dried for 16 hrs at 78° C. to yield the title compound, mpt. 119°-120.5° C. Anal. Calcd. for C10H13N5O2S: C, 44.93; H, 4.9; N, 26.20. Found: C, 44.97, H, 4.96; N, 26.17. 1H NMR in DMSO 6 8.59 (1HS), 8.15 (1Hs), 6.52 (2H broad s) 5.26 (2Hs), 4.15 (2Ht J=6.36 Hz), 2.89 (2Ht J=6.36 Hz), 1.99 (3Hs).

Workup

  1. customA 100 ml flask equipped with a magnetic stirring bar and a CaCl2 drying tube
  2. customquenched with 5 ml of MeOH
  3. customThe solution was evaporated in vacuo (bath temp 40° C.)
  4. customthe brown oil so obtained
  5. customchromatographed
  6. washElution of the column with 1.5% methanol in ethyl acetate
  7. customprovided a yellow oil which
  8. customcrystallized
  9. dissolutionThe light yellow crystals were dissolved in a solution of 2% MeOH in toluene
  10. additiontreated with 0.05 g Darco G-60
  11. customThe methanol was evaporated from the toluene solution
  12. customresulting in the precipitation of light yellow crystals
  13. customThe product was dried for 16 hrs at 78° C.

Sources & evidence

ORD record
ord-013aebf7fbdd4170b6f52268eb77982b
Source dataset
uspto-grants-1986_09
Patent number
US04609662

Reaction notes

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