Dimethylformamide → N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N,N',N'-trimethylthiourea

HRID 1668388Notes

Reaction equation

HRID 1668388 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25](CNC)=[CH:24][CH:23]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1.[CH3:31][N:32]([CH3:36])[C:33](Cl)=[S:34].[CH2:37]([N:39](CC)[CH2:40]C)C.CN(C)C=O>C(OCC)(=O)C.S([O-])(O)(=O)=O.[K+]>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][C:25]([CH2:31][N:32]([CH3:36])[C:33]([N:39]([CH3:40])[CH3:37])=[S:34])=[CH:26][CH:27]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27871Dimethylthiocarbamoyl chlorideHCID 673596986-(4-chlorophenyl)-3-(2-{4-[(methylamino)methyl]phenyl}ethyl)thieno[3,2-d]pyrimidin-4(3H)-one dihydrochloride

Product 1

HCID 11999424N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N,N',N'-trimethylthioureaYield 39.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516920Potassium bisulfateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of the compound (0.1 g) obtained in Example 4, dimethylcarbamothioyl chloride (25 mg), triethylamine (76 mg) and N,N-dimethylformamide (2 ml) was stirred at 60° C. for 3 hr. The reaction mixture was diluted with ethyl acetate, 5% aqueous potassium hydrogen sulfate solution, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and is concentrated under reduced pressure. The residue was purified by column chromatography [developing solvent:ethyl acetate-hexane (3:1, volume ratio)], and recrystallized from ethyl acetate-hexane (1:1, volume ratio) to give the title compound (40 mg) as a colorless powder.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationis concentrated under reduced pressure
  4. customThe residue was purified by column chromatography [developing solvent:ethyl acetate-hexane (3:1, volume ratio)]
  5. customrecrystallized from ethyl acetate-hexane (1:1, volume ratio)

Sources & evidence

ORD record
ord-6eec38c3d55a4051b7d7acf21c16c250
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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