Diisopropylethylamine → 2-(6-(4-(3,4-dichlorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxo thieno[2,3-d]pyrimidin-3(4H)-yl)-N,N-diethylacetamide

HRID 1094702Notes

Reaction equation

HRID 1094702 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[C:4](=[O:20])[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[C:13]([CH3:19])=[C:14]([C:16]([OH:18])=O)[S:15][C:9]=2[N:8]=[CH:7]1)[CH3:2].CCN(C(C)C)C(C)C.[Cl:32][C:33]1[CH:34]=[C:35]([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH:36]=[CH:37][C:38]=1[Cl:39].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Cl:32][C:33]1[CH:34]=[C:35]([N:40]2[CH2:45][CH2:44][N:43]([C:16]([C:14]3[S:15][C:9]4[N:8]=[CH:7][N:6]([CH2:5][C:4]([N:3]([CH2:1][CH3:2])[CH2:21][CH3:22])=[O:20])[C:11](=[O:12])[C:10]=4[C:13]=3[CH3:19])=[O:18])[CH2:42][CH2:41]2)[CH:36]=[CH:37][C:38]=1[Cl:39]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 936011-(3,4-Dichlorophenyl)piperazineHCID 44267003-(2-(Diethylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 251155632-(6-(4-(3,4-dichlorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxo thieno[2,3-d]pyrimidin-3(4H)-yl)-N,N-diethylacetamideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-(2-(diethylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid (0.12 g, 0.37 mmol) in DCM (5 mL) was added DIEA (0.2 mL, 1.1 mmol), 4(3,4-dichlorophenyl)piperazine (0.073 g, 0.37 mmol), and HATU (0.182 g, 0.48 mmol). The reaction mixture was stirred at RT overnight. The organic layer was diluted with CH2Cl2 and then washed with sat. NaHCO3 aq. (20 mL), dried over Na2SO4, and concentrated to give crude product as a gummy solid. Purification by flash column chromatography using a mixture of Et2O: DCM (1:1) as the eluant afforded the 0.092 g of 2-(6-(4-(3,4-dichlorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxo thieno[2,3-d]pyrimidin-3(4H)-yl)-N,N-diethylacetamide, (yield: 50%).

Workup

  1. washwashed with sat. NaHCO3 aq. (20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give crude product as a gummy solid
  5. customPurification by flash column chromatography
  6. additiona mixture of Et2O: DCM (1:1) as the eluant

Sources & evidence

ORD record
ord-e362c6d343014a1d83552008133bc38f
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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