Dimethylformamide → HCID 59351621, compound

HRID 1889336Notes

Reaction equation

HRID 1889336 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:11][CH:10]=2)[C:6]2[S:23][CH:24]=[CH:25][C:5]=2[C:4](=[O:26])[N:3]1[CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.P(Cl)(Cl)(Cl)=O.CN(C)[CH:42]=[O:43]>C(Cl)(Cl)Cl>[CH:42]([C:24]1[S:23][C:6]2[N:7]([CH2:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]4[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=4)=[CH:11][CH:10]=3)[C:2](=[O:1])[N:3]([CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:4](=[O:26])[C:5]=2[CH:25]=1)=[O:43]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 59351619HCID 59351619, compound

Product 1

HCID 59351621HCID 59351621, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4′-{[2,4-dioxo-3-(2-phenylethyl)-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (2 g), phosphorus oxychloride (30 mL) and N,N-dimethylformamide (10 mL) was stirred at 50° C. for 2 hr. The reaction mixture was diluted with chloroform, washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as a colorless solid (1.96 g, 92%).

Workup

  1. washwashed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-e9284ee6bd04435196cd199f4467c0bc
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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