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Chloroform → 2-Amino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)adenine

HRID 1448994
Notes
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Reaction equation

HRID 1448994 reaction equation
[N:1]([C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@@H:13]2[O:33][C@H:32]([CH2:34][O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@@H:23]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:14]2[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([N:43]=[N+]=[N-])[N:5]=1)=[N+]=[N-].C(Cl)(Cl)Cl>CCO.[Pd]>[NH2:1][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@@H:13]2[O:33][C@H:32]([CH2:34][O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@@H:23]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:14]2[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([NH2:43])[N:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6212ChloroformHCID 542955292,6-diazido-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine

Product 1

HCID 108969412-Amino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)adenineYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702Ethanol
Solvent
3×

Procedure

Pd-C (5%) (500 mg) was added to a solution of 2,6-diazido-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine (IV, 4.8 g, 8.0 mmol) in EtOH (500 ml), and the resulting mixture was hydrogenated at atmospheric pressure for 6 hr. The H2 atmosphere was changed after 30 min. and after 1 hr. The catalyst was removed by filtration and was washed with CHCl3 to dissolve precipitated product. The combined filtrate and washings were evaporated to dryness in vacuo, and the resulting residue was dissolved in boiling EtOH (80 ml). The crystals that formed on cooling the EtOH solution were collected by filtration, washed with EtOH, and dried in vacuo; yield 3.3 g (75%), mp 161°-162°, TLC (19:1 CHCl3 --MeOH). The analytically pure produce was obtained from a previous preparation: yield 69%; mp 162°; [α]D25 +44.4±0.7° (c, 1.06, CHCl3); λmax ]Mμ (ε× 10-3)], pH 1--254 (10.9), 292 (9.0); EtOH--256 (10.8), 283 (9.0); pH 7, 13--256 (9.0), 279 (9.1); vmax (cm-1)3460, 3350, 3310, 3140 (NH, CH), 2940, 2915 2890, 2865 (CH), 1660 (NH), 1590 (C=C, C=N), 1085, 1045, 1015 (COC), 730, 690 (phenyl).

Workup

  1. waitThe H2 atmosphere was changed after 30 min. and after 1 hr
  2. customThe catalyst was removed by filtration
  3. washwas washed with CHCl3
  4. dissolutionto dissolve
  5. customprecipitated product
  6. customThe combined filtrate and washings were evaporated to dryness in vacuo
  7. dissolutionthe resulting residue was dissolved
  8. customThe crystals that formed
  9. filtrationwere collected by filtration
  10. washwashed with EtOH
  11. customdried in vacuo
  12. customThe analytically pure produce
  13. customwas obtained from a previous preparation

Sources & evidence

ORD record
ord-0d4b1e64d6ae4aa69f63a8eb55393e86
Source dataset
uspto-grants-1980_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04188378

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes