Sodium Hydroxide → 4-amino-5-(methylamino)quinazolin-2(1H)-one

HRID 711761ノート

反応式

HRID 711761 の反応式
[C:1]([C:3]1[C:8]([NH:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:11][C:12]([NH:14]C(=O)C1C=CC=CC=1)=[O:13])#[N:2].[OH-].[Na+]>CCO>[NH2:2][C:1]1[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH:9][CH3:10])[NH:11][C:12](=[O:13])[N:14]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 67401506N-(2-cyano-3-(methylamino)phenylcarbamoyl)benzamide

生成物 1

HCID 251528124-amino-5-(methylamino)quinazolin-2(1H)-one収率 56.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of N-(2-cyano-3-(methylamino)phenylcarbamoyl)benzamide (Example 157a) (0.05 g, 0.17 mmol) and NaOH (2N, 0.17 mL) in EtOH (6 mL) was stirred at 90° C. under nitrogen for half an hour. The reaction mixture was cooled down to room temperature, and concentrated under vacuum. H2O (1 mL) was added and the reaction mixture was neutralized to pH˜4 with 10% AcOH. The resultant precipitation was filtered and dried under vacuum. The crude product was purified by preparative thin layer chromatography using a DCM/MeOH (9:1) solution as eluant, to give 4-amino-5-(methylamino)quinazolin-2(1H)-one (18.2 mg, 56%). 1H NMR (400 MHz, DMSO-d6) δ 2.76 (s, 3H), 6.10 (d, J=7.6 Hz, 1H), 6.12 (d, J=8 Hz, 1H), 7.13 (t, J=8 Hz, 1H), 7.25 (bs, NH), 9.66 (bs, NH) 10.13 (bs, 2H). MS 191 (MH+).

後処理

  1. concentrationconcentrated under vacuum
  2. additionH2O (1 mL) was added
  3. customThe resultant precipitation
  4. filtrationwas filtered
  5. customdried under vacuum
  6. customThe crude product was purified by preparative thin layer chromatography

出典と根拠

ORDレコード
ord-474ebe9daace4a0695be7681de058eeb
出典データセット
uspto-grants-2015_11
特許番号
US09181276B2

反応ノート

読み込み中…