Triethylamine → 1-(Methylthiomethyl)-6-phenylthiothymine

HRID 2210899

Reaction equation

HRID 2210899 reaction equation
Cl[CH2:2][S:3][CH3:4].[C:5]1([C:11]2[NH:16][C:15](=[S:17])[NH:14][C:13](=[O:18])[C:12]=2[CH3:19])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C>CN(C)C=O>[CH3:4][S:3][CH2:2][N:16]1[C:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[C:12]([CH3:19])[C:13](=[O:18])[NH:14][C:15]1=[S:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16916Chloromethyl methyl sulfideHCID 186710275-Methyl-6-phenyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one

Product 1

HCID 538403951-(Methylthiomethyl)-6-phenylthiothymineYield 8.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4 ml of dimethylformamide, 0.17 ml (2.0 mmol) of chloromethylmethylsulfide, 0.47 g (2.0 mmol) of 6-phenylthiothymine, 0.56 ml (2.0 mmol) of triethylamine were added and allowed to react for 22 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was adsorbed on a silica gel column and eluted with chloroform. The eluate was concentrated and crystallized from ethyl acetate to obtain 45 mg of the target compound (Yield: 8%).

Workup

  1. customto react for 22 hours at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washeluted with chloroform
  4. concentrationThe eluate was concentrated
  5. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5ca7112b5bda41a4b4713ca3e693ec49
Source dataset
uspto-grants-1995_10
Patent number
US05461060

Linked notes

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