Trimethylamine → 3-(4-amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide

HRID 1485488ノート

反応式

HRID 1485488 の反応式
[NH2:1][C:2]1[C:3]2[S:11][CH:10]=[C:9]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([OH:17])=O)[C:4]=2[N:5]=[C:6]([Cl:8])[N:7]=1.Cl.CN.[CH2:24]([N:26]=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.CN(C)C>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]2[S:11][CH:10]=[C:9]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([NH:26][CH3:24])=[O:17])[C:4]=2[N:5]=[C:6]([Cl:8])[N:7]=1

参加物

8

反応物 5

HCID 1146TrimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6364545Methylamine hydrochlorideHCID 866756513-(4-Amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)benzoic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 866756523-(4-amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide収率 89.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-(4-Amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)benzoic acid (300 mg, 0.98 mmol) was dissolved in N,N-dimethylformamide (5 mL) and then methylamine hydrochloride (329 mg, 4.91 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (282 mg, 1.47 mmol), hydroxybenzotriazole (239 mg, 1.76 mmol) and trimethylamine (0.889 mL, 6.38 mmol) were added. The reaction mixture was stirred at room temperature for a day. The reaction mixture was diluted with ethyl acetate and then washed with ammonium chloride aqueous solution. The organic layer was dried with magnesium sulfate, filtered with celite and then concentrated. Purification by chromatography (1/4 ethyl acetate/hexane) yielded the target compound (280 mg, 89% yield).

後処理

  1. washwashed with ammonium chloride aqueous solution
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered with celite
  4. concentrationconcentrated
  5. customPurification by chromatography (1/4 ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-cddbe8c3fc1f4e6f89228ca4466d3637
出典データセット
uspto-grants-2016_08
特許番号
US09422307B2

反応ノート

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