Sodium Azide → 6-Azido-7H-purin-2-amine

HRID 1646664Notes

Reaction equation

HRID 1646664 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[NH2:5][C:6]1[N:14]=[C:13]2[C:9]([NH:10][CH:11]=[N:12]2)=[C:8](Cl)[N:7]=1>O.CS(C)=O>[NH2:5][C:6]1[N:14]=[C:13]2[C:9]([NH:10][CH:11]=[N:12]2)=[C:8]([N:1]=[N+:2]=[N-:3])[N:7]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 53603492-Amino-6-chloropurine

Product 1

HCID 197576806-Azido-7H-purin-2-amineYield 89.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium azide (14.08 g, 0.216 mol) in water (35 mL) was added to a solution of 2-amino-6-chloropurine (28.27 g, 0.166 mol) in dimethyl sulfoxide (DMSO, 280 mL). The mixture was heated at 100°-110° C. for 24 h, then the resulting suspension was cooled and poured into 1.3 L of water. The precipitate was collected by filtration, washed with water and dried to afford 26.11 g of 2-amino-6-azidopurine, mp>260° C.; IR (KBr) 3313, 3146, 1678, 1641, 1551 cm-1 ; 1H NMR (DMSO-d6, 360 MHz) δ8.18 (s, 1H), 8.25 (bs, 2H), 13 (vbs, 1H); 13C NMR (DMSO-d6, 90 MHz), 110.8, 138.7, 143.4, 145.7 , 146.1 ppm.

Workup

  1. temperatureThe mixture was heated at 100°-110° C. for 24 h
  2. temperaturethe resulting suspension was cooled
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b0fdb8a78fd44286a0c1e3f21f30d1e1
Source dataset
uspto-grants-1993_01
Patent number
US05180824

Reaction notes

Loading…