Chlorotrimethylsilane → HCID 131720209, compound

HRID 381693Notes

Reaction equation

HRID 381693 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.[NH4+].[OH-]>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 (2.0 ml, 15.75 mmol), and stirring continued for 15 min. Benzoyl chloride (2.18 ml, 18.9 mmol) was added to the solution followed by stirring for 2 hr. The mixture was then cooled in an ice-bath and MeOH (10 ml) was added. After 5 mins., NH4OH (20 ml, 30% aq.) was added and the mixture stirred for 30 min. The reaction mixture was then concentrated under vacuum and the residue purified by short silica gel (70 g) column chromatography. Elution with CH2Cl2:MeOH (9:1, v/v), pooling of 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 hr
  2. temperatureThe mixture was then cooled in an ice-bath
  3. waitAfter 5 mins
  4. stirringthe mixture stirred for 30 min
  5. concentrationThe reaction mixture was then concentrated under vacuum
  6. customthe residue purified by short silica gel (70 g) column chromatography
  7. washElution with CH2Cl2:MeOH (9:1
  8. customv/v), pooling of appropriate fractions and evaporation

Sources & evidence

ORD record
ord-78bf1aa5a31e43498011b9b437437fc6
Source dataset
uspto-grants-2001_10
Patent number
US06307040B1

Reaction notes

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