Ammonia → HCID 54122131, compound

HRID 36001Notes

Reaction equation

HRID 36001 reaction equation
[C@@H:1]1([N:9]2[C:19]3[N:18]=[C:16]([NH2:17])[NH:15][C:13](=O)[C:12]=3[N:11]=[CH:10]2)[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH3:33]>N1C=CC=CC=1>[NH2:17][C:16]1[N:18]=[C:19]2[C:12]([N:11]=[CH:10][N:9]2[CH:1]2[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]2)=[C:13]([NH2:33])[N:15]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 9845Trifluoroacetic anhydrideHCID 135398592Deoxyguanosine

Product 1

HCID 54122131HCID 54122131, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To 2 mmol of deoxyguanosine, dried by evaporation of pyridine and suspended in 20 mL of dry pyridine was added dropwise 2.3 mL (16 mmol) of trifluoroacetic anhydride, with cooling in an ice bath. After ten minutes 20 mL of cold, concentrated aqueous ammonia was added. After a further 11/2 hours the mixture was evaporated to dryness, the residue dissolved in water and the solution filtered through a 100 mL portion of Bio Rad AG 1-X2, hydroxide from resin to remove colored impurities. The resin was washed with 40% methanol in water to elute crude 2,6-diamino-9-(2-deoxy-Beta-D-erythro-pentofuranosyl)purine, which was further purified on the reversed-phase column described above using a gradient of 2-15% acetonitrile in water. Evaporation of appropriate fractions gave 192 mg (34%) of 2,6-diamino-9-(2-deoxy-D-erythro-pentofuranosyl)purine, a sample crystallized from water gave a mp of 148°. UVmax (MeOH) 282 nm, UVmin 256 nm; 1H NMR (DMSO-d6) delta (ppm) 7.91 (s, 1,H8), 6.73 (br s, 2, NH2), 6.17 ("t", 1, Japp =6 Hz, H1'), 5.73 (br s, 2, NH2), 5.25 (m, 2, 3'-OH & 5'-OH), 4.35 (m, 1, H3'), 3.84 (m, 1, H4'), 3.54 (m,2,H5',5"), 2.59 & 2.17 (m & m, 1 & 1, H2' & H2"). Anal. Calcd. for C10H14N6O3.H2O: C, 42.25; H, 5.67; N, 29,56. Found: C, 42.54; H, 5.33; N, 29.56.

Workup

  1. temperaturewith cooling in an ice bath
  2. customAfter a further 11/2 hours the mixture was evaporated to dryness
  3. dissolutionthe residue dissolved in water
  4. filtrationthe solution filtered through a 100 mL portion of Bio Rad AG 1-X2, hydroxide from resin
  5. customto remove colored impurities
  6. washThe resin was washed with 40% methanol in water
  7. washto elute crude 2,6-diamino-9-(2-deoxy-Beta-D-erythro-pentofuranosyl)purine, which
  8. customwas further purified on the reversed-phase column
  9. customEvaporation of appropriate fractions

Sources & evidence

ORD record
ord-bc36062f3ef247629c92dd712a9817d5
Source dataset
uspto-grants-1995_05
Patent number
US05412088

Reaction notes

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