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

HRID 920662ノート

反応式

HRID 920662 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
170 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-2c45cc994563467b8e682c133669308f
出典データセット
uspto-grants-2016_03
特許番号
US09273056B2

反応ノート

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