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Dimethylformamide dimethyl acetal → 6-(4-Chlorophenyl)-3-[3-methoxy-4-(2-methyl-2-pyrrolidin-1-ylpropoxy)phenyl]thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1181354
ノート
印刷プレビュー

反応式

HRID 1181354 の反応式
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([O:16]C)=O.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]([CH3:36])([N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)[CH3:30])[NH2:23].[CH3:37]N(C(OC)OC)C>C(O)C>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:14](=[O:16])[N:23]([C:22]4[CH:24]=[CH:25][C:26]([O:27][CH2:28][C:29]([CH3:36])([N:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)[CH3:30])=[C:20]([O:19][CH3:18])[CH:21]=4)[CH:37]=[N:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1
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

5

反応物 3

HCID 78373Dimethylformamide dimethyl acetalHCID 2777492Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylateHCID 589808333-Methoxy-4-(2-methyl-2-pyrrolidin-1-ylpropoxy)aniline

生成物 1

HCID 589808306-(4-Chlorophenyl)-3-[3-methoxy-4-(2-methyl-2-pyrrolidin-1-ylpropoxy)phenyl]thieno[3,2-d]pyrimidin-4(3H)-one収率 8%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

反応条件

温度
110 °C

実験手順

Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate (0.639 g, 0.2390 mmol) was taken up in DMF-DMA (3 mL) and heated to 110° C. The reaction was stirred for 3 h and then concentrated. 3-Methoxy-4-(2-methyl-2-pyrrolidin-1-ylpropoxy)aniline (0.0631 g, 0.2390 mmol) in absolute ethanol (3 mL) was added to the residue and the mixture was then concentrated. Fresh absolute ethanol (1 mL) was added and the reaction heated to reflux. The reaction was stirred for 18 h and then cooled to RT and the precipitate was collected to give 0.010 g (0.020 mmol, 8%) of the product as a white solid. 1H NMR (CDCl3) δ 8.15 (s, 1H), 7.65 (d, 2H, J=8.3 Hz), 7.53 (s, 1H), 7.44 (d, 2H, J=8.5 Hz), 7.18 (d, 1H, J=8.3 Hz), 6.96 (s, 1H), 6.88 (d, 1H, J=8.3 Hz), 3.83 (s, 3H, 2.77 (s, 2H), 2.72 (bs, 4H), 1.78 (bs, 4H), 1.36 (s, 6H).

後処理

  1. concentrationconcentrated
  2. concentrationthe mixture was then concentrated
  3. additionFresh absolute ethanol (1 mL) was added
  4. temperaturethe reaction heated to reflux
  5. stirringThe reaction was stirred for 18 h
  6. temperaturecooled to RT
  7. customthe precipitate was collected

出典と根拠

ORDレコード
ord-f1d72c610b6749edae904cb1b00aed08
出典データセット
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07285557B2

反応ノート

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