Methanol → HCID 44413521, compound

HRID 1818664Notes

Reaction equation

HRID 1818664 reaction equation
[C:1]1([Si:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C@@H:21]1([N:29]2[CH:36]=[CH:35][C:33](=[O:34])[NH:32][C:30]2=[O:31])[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([OH:24])[CH2:22]1.CO>N1C=CC=CC=1.C(Cl)(Cl)Cl>[C:1]1([Si:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:27][CH2:26][C@H:25]2[O:28][C@@H:21]([N:29]3[CH:36]=[CH:35][C:33](=[O:34])[NH:32][C:30]3=[O:31])[CH2:22][C@@H:23]2[OH:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)HCID 13712Deoxyuridine

Product 1

HCID 44413521HCID 44413521, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6212ChloroformSolvent

Procedure

A solution of triphenylsilyl chloride (0.437 g, 1.48 mmol) in dry pyridine (4 mL) was added drop-wise to a solution of 2′-deoxyuridine (0.278 g, 1.22 mmol) in dry pyridine (4 mL) previously cooled in an ice-salt bath. The reaction mixture was kept at 0° C. for 1 h. The reaction was monitored by TLC (10% CH3OH in CHCl3) and quenched with CH3OH (50 L). The solvent was removed under reduced pressure to give a crude yellow liquid which was further purified by silica gel column chromatography (Isolute SI column) using a gradient elution of 0→10% CH3OH in CHCl3. The fractions with Rf=0.30 (10% CH3OH/CHCl3) were combined and concentrated to yield the title compound as a white crystalline solid (0.506 g, 85%).

Workup

  1. temperaturepreviously cooled in an ice-salt bath
  2. customquenched with CH3OH (50 L)
  3. customThe solvent was removed under reduced pressure
  4. customto give a crude yellow liquid which
  5. customwas further purified by silica gel column chromatography (Isolute SI column)
  6. washa gradient elution of 0→10% CH3OH in CHCl3
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-db4b99ba618b4f36bc8c39b914a82eba
Source dataset
uspto-grants-2009_10
Patent number
US07601702B2

Reaction notes

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