Benzyl Bromide → HCID 21661551, compound

HRID 2210900Notes

Reaction equation

HRID 2210900 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:12]([CH3:13])[C:10](=[O:11])[NH:9][C:7]1=[S:8].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(C(C)C)C(C)C)C>CN(C)C=O>[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:12]([CH3:13])[C:10](=[O:11])[N:9]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:7]1=[S:8]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 23168033HCID 23168033, compound

Product 1

HCID 21661551HCID 21661551, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2 ml of dimethylformamide, 0.62 g (2.0 mmol) of 1-[(2-hydroxyethoxy)methyl]-6-phenylthiothymine, 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% methanol/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% methanol/chloroform

Sources & evidence

ORD record
ord-43346f65921940d29727c8864ac01088
Source dataset
uspto-grants-1995_10
Patent number
US05461060

Reaction notes

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