1-(3-Chlorophenyl)piperazine monohydrochloride → 6-{[4-(3-Chlorophenyl)piperazino]carbonyl}-5-methylthieno[2,3-D]pyrimidin-4(3H)-one

HRID 1094723ノート

反応式

HRID 1094723 の反応式
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:12]([OH:14])=O.CCN(C(C)C)C(C)C.Cl.[Cl:25][C:26]1[CH:27]=[C:28]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:29]=[CH:30][CH:31]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[Cl:25][C:26]1[CH:27]=[C:28]([N:32]2[CH2:37][CH2:36][N:35]([C:12]([C:3]3[S:4][C:5]4[N:6]=[CH:7][NH:8][C:9](=[O:11])[C:10]=4[C:2]=3[CH3:1])=[O:14])[CH2:34][CH2:33]2)[CH:29]=[CH:30][CH:31]=1

参加物

7

反応物 4

HCID 256811-(3-Chlorophenyl)piperazine monohydrochlorideHCID 81531DiisopropylethylamineHCID 4058025-methyl-4-oxo-3H,4H-thieno[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)

生成物 1

HCID 41967806-{[4-(3-Chlorophenyl)piperazino]carbonyl}-5-methylthieno[2,3-D]pyrimidin-4(3H)-one収率 81.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid, (2 g, 9.5 mmol) in DMF (20 mL) was added DIEA (5 mL, 28.5 mmol), 1-(3-chlorophenyl)piperazine hydrochloride (2.2 g, 9.5 mmol), and HATU (4.7 g, 12.3 mmol). The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc (60 mL) and the organic layer was washed successively with sat. NaHCO3 aq. (50 mL) and brine (50 mL). The organic layer was separated, dried over Na2SO4, and concentrated to give crude product as a gummy solid. Purification by flash column chromatography using EtOAc as the eluent afforded the 3 g of pure 6-(4-(3-chlorophenyl)piperazine-1-carbonyl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one, (yield: 81%).

後処理

  1. washthe organic layer was washed successively with sat. NaHCO3 aq. (50 mL) and brine (50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give crude product as a gummy solid
  6. customPurification by flash column chromatography

出典と根拠

ORDレコード
ord-a17ea02172e946af9895b114d31055bb
出典データセット
uspto-grants-2012_03
特許番号
US08133998B2

反応ノート

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