Triethylamine → 9-(2-Azidoacetoxyethoxy-methyl)guanine

HRID 464594Notes

Reaction equation

HRID 464594 reaction equation
[N:1]([CH2:4][C:5](Cl)=[O:6])=[N+:2]=[N-:3].[OH:8][CH2:9][CH2:10][O:11][CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:18](=[O:22])[NH:17][C:16]([NH2:23])=[N:15][C:14]1=2.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C)C=O>[N:1]([CH2:4][C:5]([O:8][CH2:9][CH2:10][O:11][CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:18](=[O:22])[NH:17][C:16]([NH2:23])=[N:15][C:14]1=2)=[O:6])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 109095582-azidoacetyl Chloride2×HCID 135398513Acyclovir

Product 1

HCID 1361328329-(2-Azidoacetoxyethoxy-methyl)guanineYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 0.84 ml (8.4 mmol) azidoacetyl chloride in 5 ml dry dimethylformamide was added dropwise over 10 minutes in an ice-cooled, thoroughly stirred suspension of 1.25 g (5.55 mmol) 9-(2-hydroxyethoxymethyl)guanine and 0.78 ml (5.55 mmol) triethylamine in 40 ml dry dimethylformamide. After 45 minutes of thorough stirring at 0° C., 0.11 ml (1.1 mmol) azidoacetylchloride in 1 ml dimethylformamide was added, and stirring was continued for 15 minutes. The reaction was stopped by the addition of 15 ml 7% NaHCO3 solution whereupon the mixture was evaporated to dryness in vacuo. The residue was triturated with 20 ml of a mixture of methylene chloride:diethyl ether:ethanol (volume ratio 5:5:1). The solid substance obtained was filtered off, thoroughly washed with cold water and recrystallised from hot water, after treatment with active carbon. 1.02 g (62%) of 9-(2-azidoacetoxyethoxy-methyl)guanine m.p. 175°-177° C. (decomposition) was obtained. MS m/e 308 (M30), 151 (base+H); IR (KBr) 2110 (N3), 1745 (COOR) cm-1 ; UV (phosphate buffer, pH=7) λmax 253 nm (ε 8.42× 103), 270 (sh); TLC Rf 0.27 (CHCl3 --MeOH, 8:2), Rf 0.60 (EtOH--HOAc, 8:2).

Workup

  1. temperaturecooled
  2. stirringstirring
  3. waitwas continued for 15 minutes
  4. customwas evaporated to dryness in vacuo
  5. customThe residue was triturated with 20 ml of a mixture of methylene chloride
  6. customThe solid substance obtained
  7. filtrationwas filtered off
  8. washthoroughly washed with cold water
  9. customrecrystallised from hot water

Sources & evidence

ORD record
ord-0eb9109f68374344a4ffdaa4ad470786
Source dataset
uspto-grants-1985_10
Patent number
US04548819

Reaction notes

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