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

HRID 1668387Notes

Reaction equation

HRID 1668387 reaction equation
[ClH:1].Cl.Cl[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]([CH2:28][NH:29][CH3:30])=[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)=[O:34].C(N(CC)CC)C.O1CCCC1>C(OCC)(=O)C>[Cl:1][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]([CH2:28][N:29]([CH3:30])[C:33]([N:32]([CH3:36])[CH3:31])=[O:34])=[CH:24][CH:23]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 673596986-(4-chlorophenyl)-3-(2-{4-[(methylamino)methyl]phenyl}ethyl)thieno[3,2-d]pyrimidin-4(3H)-one dihydrochloride

Product 1

HCID 59239849N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N,N',N'-trimethylureaYield 70.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of the compound (0.1 g) obtained in Example 4, dimethylcarbamoyl chloride (25 mg), triethylamine (76 mg) and tetrahydrofuran (2 ml) was stirred at 60° C. for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane (1:1, volume ratio) to give the title compound (70 mg) as a colorless powder.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from ethyl acetate-hexane (1:1, volume ratio)

Sources & evidence

ORD record
ord-a8dc207569ee4730a3dedf9d259723c5
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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