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

HRID 1875502

反応式

HRID 1875502 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6213Dimethyl Sulfone溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f4f26fccdecc4a89bea282ad0bc7a48c
出典データセット
uspto-grants-2012_11
特許番号
US08309564B2

関連ノート

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