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

HRID 471625노트

반응식

HRID 471625 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-ad33fe61d5c0474f965891d2d29eae2e
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633186B2

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