Pyridine → HCID 86756709, compound

HRID 1977594Notes

Reaction equation

HRID 1977594 reaction equation
CN(C)OCC[O:6][C@@H:7]1[C@H:11]([OH:12])[C@@H:10]([CH2:13][OH:14])[O:9][C@H:8]1[N:15]1[CH:22]=[C:21]([CH3:23])[C:19](=[O:20])[NH:18][C:16]1=[O:17].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C[O:40][C:41]1[CH:62]=CC(C(Cl)(C2C=CC=CC=2)C2C=CC(OC)=CC=2)=CC=1.[N:63]1[CH:68]=CC=C[CH:64]=1>CN(C)C1C=CN=CC=1>[CH3:64][N:63]([CH3:68])[O:40][CH2:41][CH2:62][C@@:8]1([N:15]2[CH:22]=[C:21]([CH3:23])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[O:9][C@H:10]([CH2:13][OH:14])[C@@H:11]([OH:12])[C@H:7]1[OH:6]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 14812Phosphorus oxide (P4O10)HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 229476992'-O-{2-[(Dimethylamino)oxy]ethyl}-5-methyluridine

Product 1

HCID 86756709HCID 86756709, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

2′-O-(dimethylaminooxyethyl)-5-methyluridine (750 mg, 2.17 mmol) was dried over P2O5 under high vacuum overnight at 40° C. It was then co-evaporated with anhydrous pyridine (20 mL). The residue obtained was dissolved in pyridine (11 mL) under argon atmosphere. 4-dimethylaminopyridine (26.5 mg, 2.60 mmol), 4,4′-dimethoxytrityl chloride (880 mg, 2.60 mmol) was added to the mixture and the reaction mixture was stirred at room temperature until all of the starting material disappeared. Pyridine was removed under vacuum and the reside chromatographed and eluted with 10% MeOH in CH2Cl2 (containing a few drops of pyridine) to get 5′-O-DMT-2′-O-(dimethylamino-oxyethyl-5-methyluridine (1.13 g, 80%).

Workup

  1. customThe residue obtained
  2. customPyridine was removed under vacuum
  3. customthe reside chromatographed
  4. washeluted with 10% MeOH in CH2Cl2 (containing a few drops of pyridine)

Sources & evidence

ORD record
ord-3b6e12993aad4b4389218ce73c5e8378
Source dataset
uspto-grants-2001_05
Patent number
US06235723B1

Reaction notes

Loading…