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Sodium Iodide → 1-(3-(5-Chloro-2,3-dihydrospiro[indene-1,3'-pyrrolidine]-1'-yl)propyl)-5-(thiophen-2-yl)pyrimidine-2,4(1h,3h)-dione hydrochloride

HRID 1661081
ノート
印刷プレビュー

反応式

HRID 1661081 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:10]=[C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[C:8](=[O:16])[NH:7][C:6]1=[O:17].Cl.[Cl:19][C:20]1[CH:21]=[C:22]2[C:30](=[CH:31][CH:32]=1)[C:25]1([CH2:29][CH2:28][NH:27][CH2:26]1)[CH2:24][CH2:23]2.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.CN1C(=O)CCC1>[ClH:1].[Cl:19][C:20]1[CH:21]=[C:22]2[C:30](=[CH:31][CH:32]=1)[C:25]1([CH2:29][CH2:28][N:27]([CH2:2][CH2:3][CH2:4][N:5]3[CH:10]=[C:9]([C:11]4[S:12][CH:13]=[CH:14][CH:15]=4)[C:8](=[O:16])[NH:7][C:6]3=[O:17])[CH2:26]1)[CH2:24][CH2:23]2
参加物反応条件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 5238Sodium IodideHCID 11430Potassium CarbonateHCID 593375931-(3-chloropropyl)-5-(2-thienyl)-2,4(1H,3H)-pyrimidinedioneHCID 674279925-Chloro-2,3-dihydrospiro[indene-1,3'-pyrrolidine] hydrochloride

生成物 1

HCID 674297191-(3-(5-Chloro-2,3-dihydrospiro[indene-1,3'-pyrrolidine]-1'-yl)propyl)-5-(thiophen-2-yl)pyrimidine-2,4(1h,3h)-dione hydrochloride収率 81.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
70 °C

実験手順

A mixture of 1-(3-chloropropyl)-5-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione (Prep24, 50 mg, 0.18 mmol), 5-chloro-2,3-dihydrospiro[indene-1,3′-pyrrolidine]hydrochloride salt (Prep10, 66 mg, 0.27 mmol), potassium carbonate (112 mg, 0.81 mmol), sodium iodide (112 mg, 0.75 mmol) and NMP (1 ml) was stirred at 70° C. overnight. Then it was cooled down to room temperature and diluted with water and extracted with ethyl acetate. The EA phase was evaporated and the crude purified by preparative TLC (TLC analysis performed by eluting with EA/MeOH 10:1) to give the free base of the title compound (70 mg). The compound was purified by preparative HPLC and treated with a 1N solution of HCl-ether to give the title compound (9 mg, y=10%).

後処理

  1. temperatureThen it was cooled down to room temperature
  2. extractionextracted with ethyl acetate
  3. customThe EA phase was evaporated
  4. customthe crude purified by preparative TLC (TLC analysis performed by eluting with EA/MeOH 10:1)

出典と根拠

ORDレコード
ord-3b11f6e5cd354543a48dc77cdd1079c6
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08030322B2

反応ノート

読み込み中…

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