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Triethylamine → 6-(4-fluorophenyl)-3-{2-[4-(1-pyrrolidin-1-ylethyl)phenyl]ethyl}thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione

HRID 1668399
ノート
印刷プレビュー

反応式

HRID 1668399 の反応式
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[CH3:26])=[CH:21][CH:20]=1)=[O:15].C(N(CC)CC)C.Cl[C:40](Cl)([O:42]C(=O)OC(Cl)(Cl)Cl)Cl.N1CCCC1>ClCCCl.C(OCC)(=O)C>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[S:4][C:3]3[C:14](=[O:15])[N:16]([CH2:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([CH:25]([N:27]5[CH2:31][CH2:30][CH2:29][CH2:28]5)[CH3:26])=[CH:21][CH:20]=4)[C:40](=[O:42])[NH:1][C:2]=3[CH:6]=2)=[CH:8][CH:9]=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 8471TriethylamineHCID 31268PyrrolidineHCID 94429TriphosgeneHCID 673594643-amino-5-(4-fluorophenyl)-N-{2-[4-(1-pyrrolidin-1-ylethyl)phenyl]ethyl}thiophene-2-carboxamide

生成物 1

HCID 592398686-(4-fluorophenyl)-3-{2-[4-(1-pyrrolidin-1-ylethyl)phenyl]ethyl}thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione収率 19.2%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The obtained 3-amino-5-(4-fluorophenyl)-N-{2-[4-(1-pyrrolidin-1-ylethyl)phenyl]ethyl}thiophene-2-carboxamide (0.15 g) was suspended in 1,2-dichloroethane (5 ml), and triethylamine (0.067 ml) and triphosgene (0.080 g) were successively added with stirring. After 3 hr, pyrrolidine (0.8 ml) was added, and the reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (hexane:ethyl acetate=9:1 (volume ratio)→1:2 (volume ratio)) using NH-silica gel, and further recrystallized from ethyl acetate to give the title compound (0.024 g) as pale-yellow crystals.

後処理

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (hexane
  6. customfurther recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-3ef1295ccde44e2a85f5f453d428fbc3
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07989445B2

反応ノート

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