Acetic Acid → 9-(4-Thio-2,3-dideoxy-D-ribofuranosyl)-2-chloro-6aminopurine

HRID 653985Notes

Reaction equation

HRID 653985 reaction equation
[Si]([O:18][CH2:19][C@H:20]1[S:24][CH:23]([N:25]2[CH:33]=[N:32][C:31]3[C:26]2=[N:27][C:28]([Cl:35])=[N:29][C:30]=3[NH2:34])[CH2:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CC(O)=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>C1COCC1.N1C=CC=CC=1>[CH:23]1([N:25]2[CH:33]=[N:32][C:31]3[C:26]2=[N:27][C:28]([Cl:35])=[N:29][C:30]=3[NH2:34])[S:24][C@H:20]([CH2:19][OH:18])[CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 2724141Tetrabutylammonium FluorideHCID 15126104HCID 15126104, compound

Product 1

HCID 151261069-(4-Thio-2,3-dideoxy-D-ribofuranosyl)-2-chloro-6aminopurineYield 70%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 15 (100 mg, 0.19 mmol) in 5 mL of THF was added CH3COOH (14 μL, 0.24 mmol) and 1 M solution of tetrabutylammonium fluoride in MeOH (0.4 mL, 0.4 mmol) followed by stirring for 1 hour. One drop of pyridine was added and then solvent was evaporated in vacuo. The residue was purified by preparative TLC using 90:10 CHCl3 -MeOH as eluant to afford crude 18 which was crystallized by EtOH to give pure 18 (38 mg, 70%); mp. 125°-127° C.; FAB MS 286 (M+H)+ ; 1H NMR (DMSO-d6) δ 8.45 (s, 1, H-2), 7.80 (brs, 2, NH2), 6.10 (m, 1, 1'-H), 5.12 (m, 1, 5'-OH), 3.75 (m, 1, 4'-H), 3.61 (m, 2, 5'-H), 2.40 (m, 2, 2'-H), 2.15 (m, 1, 3'-H), 2.0 (m, 1, 3'-H).

Workup

  1. customsolvent was evaporated in vacuo
  2. customThe residue was purified by preparative TLC
  3. customto afford crude 18 which
  4. customwas crystallized by EtOH

Sources & evidence

ORD record
ord-a8a034126f4d42c0b1f241c366ff233e
Source dataset
uspto-grants-1992_07
Patent number
US05128458

Reaction notes

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