Ammonia → HCID 13869780, compound

HRID 1461519Notes

Reaction equation

HRID 1461519 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]2[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15][CH2:14]2)=[C:4]([N:21]=[N+]=[N-])[N:3]=1.C(O)=O.N>[Pd].CO>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]2[CH2:14][O:15][C:16]([CH3:19])([CH3:20])[O:17][CH2:18]2)=[C:4]([NH2:21])[N:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 284Formic AcidHCID 138697792-Amino-6-azido-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine

Product 1

HCID 13869780HCID 13869780, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-amino-6-azido-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (318 mg, 1.0 mmol), formic acid (0.15 ml, 4.0 mmol), concentrated ammonia (0.22 ml, 4.0 mmol), 10% palladium-on-charcoal (30 mg) and methanol (10 ml) was heated under reflux for 1 hour. The solution was allowed to cool, filtered and the solvent removed. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol mixtures (20:1 and 15:1) to give 2,6-diamino-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (190 mg, 65%), m.p. 202°-204° C.); νmax (KBr) 1670, 1640, 1595, and 1410 cm-1 ; δH (CDCl3 -CD3OD) 1.42 (6 H, s, C(CH3)2), 1.6-2.0 (3 H, m, CHCH2CH2), 3.5-4.2 (6 H, m, 2×CH2O and CH2N), and 7.68 (1 H, s, 8-H) (Found: C, 52.88; H, 6.78; N, 28.36%; M+ 292.1652, C13H20N6O2 requires C, 53.41; H, 6.90; N, 28.75%; M+ 292.1648).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe solvent removed
  6. customThe residue was purified by column chromatography on silica gel eluting with chloroform-methanol mixtures (20:1 and 15:1)

Sources & evidence

ORD record
ord-6f12fbcc350f4bfbb61f1da83f9aab96
Source dataset
uspto-grants-1991_12
Patent number
US05075445

Reaction notes

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