Dimethylformamide → HCID 21661551, compound

HRID 1057249Notes

Reaction equation

HRID 1057249 reaction equation
CN(C)C=O.[OH:6][CH2:7][CH2:8][O:9][CH2:10][N:11]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]1=[S:13].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(C(C)C)C(C)C)C>>[OH:6][CH2:7][CH2:8][O:9][CH2:10][N:11]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:17]([CH3:18])[C:15](=[O:16])[N:14]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:12]1=[S:13]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 23168033HCID 23168033, compound

Product 1

HCID 21661551HCID 21661551, compoundYield 30%

Procedure

To 2 ml of dimethylformamide 0.62 g (2.0 mmol) of 1-[(2-hydroxyethoxy)methyl]-6-penylthiothymine, 0.26 ml (2.2 mmol) of benzyl bromide and 0.38 ml (2.2 mmol) of ethyldiisopropylamine were added and allowed to react for 5 days at room temperature under nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure and the residue was adsorbed on a silica gel column and eluted with 1% methano/chloroform to obtain 0.24 g of the target compound (Yield: 30%).

Workup

  1. customto react for 5 days at room temperature under nitrogen atmosphere
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washeluted with 1% methano/chloroform

Sources & evidence

ORD record
ord-943bfcf08c3948d68cf200f471bf7f56
Source dataset
uspto-grants-2003_02
Patent number
USRE037979E1

Reaction notes

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