Acetic Acid → 2-Amino-4-chloro-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

HRID 1356115ノート

反応式

HRID 1356115 の反応式
Cl.[NH2:2][C:3]1[N:8]=[C:7](Cl)[C:6]([CH:10]=[N:11]O)=[C:5]([Cl:13])[N:4]=1.C(O)(=[O:16])C>>[NH2:2][C:3]1[NH:8][C:7](=[O:16])[C:6]([C:10]#[N:11])=[C:5]([Cl:13])[N:4]=1

参加物

4

反応物 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 731656572-Amino-4,6-dichloro-pyrimidine-5-carbaldehyde oxime

生成物 1

HCID 1356048692-Amino-4-chloro-6-oxo-1,6-dihydropyrimidine-5-carbonitrile収率 93%

反応条件

温度
115 °C

実験手順

Following the method of Bell et al. (J. Heterocyclic Chem. 1983, 20, 41), hydrogen chloride gas was bubbled for 2 minutes though a solution of 6.00 g (29.0 mmol) 2-amino-4,6-dichloro-pyrimidine-5-carbaldehyde oxime in 800 ml acetic acid at 115° C. The mixture was then stirred at 115° C. for 16 hours before being cooled to room temperature. The resulting crystals were removed by filtration, and the filtrate concentrated in vacuo. The residue was triturated in 100 ml ether to afford 4.60 g (93%) 2-amino-4-chloro-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile as a light yellow crystalline solid. EI-MS m/e (%): 172 (M{37Cl}+, 23), 170 (M{35Cl}+, 71), 129 (53), 43 (100).

後処理

  1. temperaturebefore being cooled to room temperature
  2. customThe resulting crystals were removed by filtration
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was triturated in 100 ml ether

出典と根拠

ORDレコード
ord-13a4ebe5d7aa4fa1abad46c89552eef2
出典データセット
uspto-grants-2003_07
特許番号
US06586441B2

反応ノート

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