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Hydrochloric Acid → (3-Methyl-1H-indol-5-yl)-(6-phenyl-thieno[3,2-d]pyrimidin-4-yl)-amine

HRID 2297820
ノート
印刷プレビュー

反応式

HRID 2297820 の反応式
[C:1]1([C:7]2[S:15][C:14]3[C:13]([NH:16][C:17]4[CH:18]=[C:19]5[C:23](=[CH:24][CH:25]=4)[NH:22][CH:21]=[C:20]5[CH:26]=O)=[N:12][CH:11]=[N:10][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+].[Cl-].[NH4+].Cl>C(Cl)Cl.[I-].[Zn+2].[I-]>[CH3:26][C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[C:17]([NH:16][C:13]3[C:14]4[S:15][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[CH:8][C:9]=4[N:10]=[CH:11][N:12]=3)[CH:18]=2)[NH:22][CH:21]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 5003444Sodium cyanoborohydrideHCID 183827505-(6-Phenyl-thieno[3,2-d]pyrimidin-4-ylamino)-1H-indole-3-carbaldehyde

生成物 1

HCID 18382736(3-Methyl-1H-indol-5-yl)-(6-phenyl-thieno[3,2-d]pyrimidin-4-yl)-amine収率 31%

試薬・触媒・溶媒 2

HCID 9883512
zinc(II)iodide
触媒
HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 5-(6-phenyl-thieno[3,2-d]pyrimidin-4-ylamino)-1H-indole-3-carbaldehyde (75 mg, 0.203 mmol) in 5 mL of methylene chloride was added zinc iodide (97 mg, 0.303) and sodium cyanoborohydride (97 mg, 1.522 mmol). The reaction mixture was refluxed for 24 hours and then cooled to ambient temperature and poured into an ice-cooled mixture of saturated ammonium chloride. The solution was then neutralized with 6N HCl and extracted with ethyl acetate (3×, 50 mL). The organic extracts were dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed using a Biotage Autoflash 40 system and 1% MeOH/CH2Cl2 to produce the title compound (22 mg, 31% yield). RP18-HPLC RT: 6.071 minutes; API MS: 357.10 (M+1); MP: 221-223° C.

後処理

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate (3×, 50 mL)
  4. dry with materialThe organic extracts were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed

出典と根拠

ORDレコード
ord-722fe741585145149bbf6762e1055637
出典データセット
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06492383B1

反応ノート

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