Sodium borohydride → HCID 24896977, compound

HRID 390097Notes

Reaction equation

HRID 390097 reaction equation
I([O-])(=O)(=O)=O.[Na+].Cl.Cl.[NH2:9][C:10]1[C:11]2[NH:18][CH:17]=[C:16]([C@H:19]3[C@H:23]([OH:24])[C@H:22]([OH:25])[C@@H:21]([CH2:26][S:27][CH3:28])[NH:20]3)[C:12]=2[N:13]=[CH:14][N:15]=1.[BH4-].[Na+]>O>[NH2:9][C:10]1[C:11]2[NH:18][CH:17]=[C:16]([C@H:19]([NH:20][C@H:21]([CH2:26][S:27][CH3:28])[CH2:22][OH:25])[CH2:23][OH:24])[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 23667635Sodium periodateHCID 66953542HCID 66953542, compound

Product 1

HCID 24896977HCID 24896977, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium periodate (0.070 g, 0.326 mmol) was added to a solution of (2S,3S,4R,5S)-2-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(methylthiomethyl)pyrrolidine-3,4-diol dihydrochloride (0.1 g, 0.272 mmol, prepared according to G. B. Evans, R. H. Furneaux, V. L. Schramm, V. Singh, P. C. Tyler, J. Med. Chem., 2004, 47, 3275) in water (3 ml) and stirred at rt for 1 h. Sodium borohydride (0.051 g, 1.358 mmol) was added in small portions (vigorous reaction). The solution, which momentarily darkened then became almost colourless, was stirred for 15 mins. Silica gel was added and the solvent evaporated. The residue was chromatographed on silica gel (CH2Cl2-MeOH-28% aq. NH4OH, 50:10:1) and the fractions containing product were evaporated to a gum (70 mg) which was dissolved in MeOH and passed through Amberlyst A26 (OH−) resin using MeOH as eluant. The solvent was evaporated to a yellow gum, dissolved in water and lyophilised to give (S)-2-((S)-1-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-2-hydroxyethylamino)-3-(methylthio)propan-1-ol as a cream coloured solid (38 mg, 47%).

Workup

  1. stirringwas stirred for 15 mins
  2. additionSilica gel was added
  3. customthe solvent evaporated
  4. customThe residue was chromatographed on silica gel (CH2Cl2-MeOH-28% aq. NH4OH, 50:10:1)
  5. additionthe fractions containing product
  6. customwere evaporated to a gum (70 mg) which
  7. dissolutionwas dissolved in MeOH
  8. customThe solvent was evaporated to a yellow gum
  9. dissolutiondissolved in water

Sources & evidence

ORD record
ord-1421ef812c0e4473a8ac0644dddbcce0
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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