Acetic Acid → 5-benzyl-6-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 855500

반응식

HRID 855500 반응식
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]([O:9]CC)=O.[C:12](OC)(OC)(OC)[CH2:13][CH2:14][CH3:15].C(O)(=O)C.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)C>[CH2:26]([N:33]1[C:7](=[O:9])[C:3]2[CH:4]=[N:5][NH:6][C:2]=2[N:1]=[C:12]1[CH2:13][CH2:14][CH3:15])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 81472ethyl 3-amino-1H-pyrazole-4-carboxylateHCID 1235121,1,1-Trimethoxybutane

생성물 1

HCID 589354415-benzyl-6-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

A mixture of ethyl 5-amino-1H-pyrazole-4-carboxylate (1-1, 3.1 g, 20 mmol, 1 equiv), trimethyl orthobutyrate (5.9 g, 40 mmol, 2 equiv) and acetic acid (120 mg, 2 mmol, 0.1 equiv) was heated at 90° C. for 3 h. Excess trimethyl orthobutyrate was removed by distillation. The residue added to a solution of benzylamine (4.2 g, 40 mmol, 2 equiv) in ethanol (25 mL), and the resulting solution was heated at reflux for 18 h, then cooled and concentrated. The residue was triturated with EtOAc to provide 5-benzyl-6-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (1-2) as a colorless solid. 1H NMR (500 MHz, CDCl3) δ 11.5 (bs, 1H), 8.19 (s, 1H), 7.34 (m, 2H), 7.28 (m, 1H), 7.15 (d, J=7 Hz, 2H), 5.41 (s, 2H), 2.75 (t, J=7 Hz, 2H), 1.82 (m, 2H), 0.99 (t, J=7 Hz, 3H).

후처리

  1. customExcess trimethyl orthobutyrate was removed by distillation
  2. temperaturethe resulting solution was heated
  3. temperatureat reflux for 18 h
  4. temperaturecooled
  5. concentrationconcentrated
  6. customThe residue was triturated with EtOAc

출처 및 근거

ORD 기록
ord-d7fecfae2ece42418e54ca3470d59695
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262186B2

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