Sodium Hydroxide → HCID 178429605、化合物

HRID 471525ノート

反応式

HRID 471525 の反応式
C([NH:9][C:10](=[O:27])[NH:11][C:12]1[S:16][C:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:14]([CH3:24])[C:13]=1[C:25]#[N:26])(=O)C1C=CC=CC=1.[OH-].[Na+]>CCO>[NH2:26][C:25]1[C:13]2[C:14]([CH3:24])=[C:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[S:16][C:12]=2[NH:11][C:10](=[O:27])[N:9]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 57456933Tert-butyl 5-(3-benzoylureido)-4-cyano-3-methylthiophene-2-carboxylate

生成物 1

HCID 178429605HCID 178429605、化合物収率 63%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspension of tert-butyl 5-(3-benzoylureido)-4-cyano-3-methylthiophene-2-carboxylate (example 64a) (18 g, 60.52 mmol) in EtOH (200 mL) was added NaOH (75 mL, 2N). The suspension became clear, and the mixture was heated to reflux for 30 min. After cooling to rt, the reaction was filtered, and the filtrate was cooled to 0° C. in an ice/water bath. The solution was neutralized with 10% acetic acid. The precipitated solid was collected by filtration, and heated in EtOH at 80° C. under N2 for 20 min. After cooling to rt, the product was collected by filtration and washed with 10% EtOH in H2O to yield tert-Butyl 4-amino-5-methyl-2-oxo-1,2-dihydrothieno[2,3-d]pyrimidine-6-carboxylate (10.73 g, 63%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 1.51 (s, 9H), 2.73 (s, 3H), 3.18 (s, 2H). MS 282.2 (MH+).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 min
  3. filtrationthe reaction was filtered
  4. temperaturethe filtrate was cooled to 0° C. in an ice/water bath
  5. filtrationThe precipitated solid was collected by filtration
  6. temperatureheated in EtOH at 80° C. under N2 for 20 min
  7. temperatureAfter cooling to rt
  8. filtrationthe product was collected by filtration
  9. washwashed with 10% EtOH in H2O

出典と根拠

ORDレコード
ord-80495de7bff047d3a878b11c533f39b4
出典データセット
uspto-grants-2014_01
特許番号
US08633186B2

反応ノート

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