Hydrochloric Acid → N-Butyl-5H-pyrrolo[3,2-d]pyrimidin-2-amine

HRID 920662

반응식

HRID 920662 반응식
Cl[C:2]1[N:3]=[CH:4][C:5]2[NH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH2:11]([NH2:15])[CH2:12][CH2:13][CH3:14].Cl>CC(O)C>[CH2:11]([NH:15][C:2]1[N:3]=[CH:4][C:5]2[NH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)[CH2:12][CH2:13][CH3:14]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 8007ButylamineHCID 457899862-Chloro-5H-pyrrolo[3,2-d]pyrimidine

생성물 1

HCID 86731154N-Butyl-5H-pyrrolo[3,2-d]pyrimidin-2-amine수율 96%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
170 °C

실험 절차

A suspension of 2-chloro-5H-pyrrolo[3,2-d]pyrimidine (0.62 g, 4 mmol) in 5 mL iPrOH was added nBuNH2 (2.5 mL, 25.3 mmol) and followed by HCl (2.0 mL, 4.0 M in dioxanes, 8 mmol). The resulting solution was heated at 170° C. for 1 h under microwave irradiation. The reaction was monitored by LC-MS. The reaction time should be extended whenever it is necessary. After evaporation of solvents, the crude product was washed with minimal amount of MeOH. The solid was collected. And the MeOH filtrate was purified by ISCO to provide the desired product (0.73 g, 96%). 1H NMR (400 MHz, CD3OD) δ 8.42 (d, J=0.8 Hz, 1H), 7.53 (d, J=3.1 Hz, 1H), 6.27 (dd, J=3.0, 0.8 Hz, 1H), 3.37 (t, J=7.1 Hz, 2H), 1.68-1.57 (m, 2H), 1.52-1.36 (m, 2H), 0.97 (t, J=7.4 Hz, 3H); MS m/z 191.2 [M+H]+.

후처리

  1. customAfter evaporation of solvents
  2. washthe crude product was washed with minimal amount of MeOH
  3. customThe solid was collected
  4. customAnd the MeOH filtrate was purified by ISCO

출처 및 근거

ORD 기록
ord-2c45cc994563467b8e682c133669308f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273056B2

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