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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
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HRID 1181354 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702
Ethanol
용매

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온도
110 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f1d72c610b6749edae904cb1b00aed08
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07285557B2

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