Water → 2-Amino-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3h)-one

HRID 1875502

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HRID 1875502 반응식
[NH2:1][C:2]1[S:3][C:4]2[CH2:15][CH2:14][CH2:13][CH2:12][C:5]=2[C:6]=1[C:7](OCC)=[O:8].ClC1C=CC=C2C=1C1C(=O)NC(NC(=O)C(C)(C)C)=[N:26][C:20]=1[NH:21]2.O.[OH-].[NH4+]>CS(C)(=O)=O>[NH2:21][C:20]1[NH:26][C:7](=[O:8])[C:6]2[C:5]3[CH2:12][CH2:13][CH2:14][CH2:15][C:4]=3[S:3][C:2]=2[N:1]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 78262Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylateHCID 135916071HCID 135916071, 화합물

생성물 1

HCID 2901972-Amino-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3h)-one수율 60%

시약·촉매·용매 1

HCID 6213Dimethyl Sulfone용매

반응 조건

온도
150 °C

실험 절차

To a 50 mL flask was added 4 (225 mg, 1 mmol), 9 (452 mg, 4 mmol) in DMSO2 (500 mg) was heated at 150° C. for 2 h. The mixture was cooled to room temperature. 15 mL water was added and ammonium hydroxide was used to neutralize the suspension. The brown solid was obtained by filtration. Washed with water and dried. The solid was dissolved in methanol and silica gel was added. A dry silica gel plug obtained after evaporation. The plug was then loaded on the column and washed with 5% methanol in chloroform. The fractions containing the desired product (TLC) were pooled and evaporated to afford 132 mg (60%) of 10 as a white solid: 1H NMR (DMSO-d6) δ 1.71 (m, 4H), 2.60 (m, 2H), 2.72 (m, 2H), 6.38 (s, 2H), 10.72 (s, 1H). Anal. calcd for C10H11N3OS: C, 54.28; H, 5.01; N, 18.99; 0, 7.23; S, 14.49. Found: C, 53.45; H, 5.06; N, 18.26; S, 14.02.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customThe brown solid was obtained by filtration
  3. washWashed with water
  4. customdried
  5. dissolutionThe solid was dissolved in methanol
  6. additionsilica gel was added
  7. customA dry silica gel plug obtained
  8. customafter evaporation
  9. washwashed with 5% methanol in chloroform
  10. additionThe fractions containing the desired product (TLC)
  11. customevaporated

출처 및 근거

ORD 기록
ord-f4f26fccdecc4a89bea282ad0bc7a48c
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309564B2

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