Chlorotrimethylsilane → HCID 131720209, compound

HRID 722764Notes

Reaction equation

HRID 722764 reaction equation
[CH3:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]1=[S:12].C[Si](C)(C)Cl.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[NH4+]>N1C=CC=CC=1.CO>[C:23]([NH:15][C:14]1[CH:16]=[CH:17][N:10]([C@@H:3]2[O:4][C@H:5]([CH2:8][OH:9])[C@@H:6]([OH:7])[C@H:2]2[CH3:1])[C:11](=[S:12])[N:13]=1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7412Benzoyl chlorideHCID 14923Ammonium HydroxideHCID 131720210HCID 131720210, compound

Product 1

HCID 131720209HCID 131720209, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

To a stirred solution of 2′-deoxy-2′-methylthiocytidine (0.86 g, 3.15 mmol) in dry pyridine (20 mL) was added trimethylchlorosilane (2 mL, 15.75 mmol), and stirring continued for 15 minutes. Benzoyl chloride (2.18 mL, 18.9 mmol) was added to the solution followed by stirring for 2 hours. The mixture was then cooled in an ice bath and MeOH (10 mL) was added. After 5 minutes, ammonium hydroxide (30% aq., 20 mL) was added and the mixture stirred for 30 minutes. The reaction mixture was then concentrated under reduced pressure and the residue purified by short silica gel (70 g) column chromatography. Elution with CH2Cl2—MeOH (9:1), pooling of the appropriate fractions and evaporation furnished the title compound (0.55 g, 46.6%), which crystallized from EtOH as needles, m.p. 193–194° C.

Workup

  1. stirringby stirring for 2 hours
  2. temperatureThe mixture was then cooled in an ice bath
  3. waitAfter 5 minutes
  4. stirringthe mixture stirred for 30 minutes
  5. concentrationThe reaction mixture was then concentrated under reduced pressure
  6. customthe residue purified by short silica gel (70 g) column chromatography
  7. washElution
  8. customwith CH2Cl2—MeOH (9:1), pooling of the appropriate fractions and evaporation

Sources & evidence

ORD record
ord-e752582a96a54a6092c53710d3d41161
Source dataset
uspto-grants-2006_11
Patent number
US07138517B2

Reaction notes

Loading…