Phosphorus oxychloride → HCID 18507370、化合物

HRID 1355722ノート

反応式

HRID 1355722 の反応式
[NH2:1][C:2]1[NH:3][C:4](=O)[C:5]([C:14]#[N:15])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.P(Cl)(Cl)([Cl:19])=O>>[NH2:1][C:2]1[N:3]=[C:4]([Cl:19])[C:5]([C:14]#[N:15])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 1357249972-Amino-4-oxo-6-phenyl-1,4-dihydro-5-pyrimidinecarbonitrile

生成物 1

HCID 18507370HCID 18507370、化合物収率 44%

反応条件

温度
70 °C

実験手順

Following the method of Hull (J. Chem. Soc. 1957, 4845), a stirred suspension of 25.2 g (119 mmol) 2-amino-6-oxo-4-phenyl-1,6-dihydro-pyrimidine-5-carbonitrile in 27.1 ml (297 mmol) phosphorus oxychloride was heated at reflux for 2 h. The reaction mixture was then cooled to about 70° C. and poured cautiously onto rapidly stirred ice-water such that the temperature remained around 10° C. The resulting crystals were collected by filtration to afford 12.0 g (44%) 2-amino-4-chloro-6-phenyl-pyrimidine-5-carbonitrile as a light beige crystalline solid. This material was pure enough to be used in subsequent steps, however analytically pure material was obtained by chromatography (ethyl acetate/hexane 1/1) which afforded 5.9 g (22%) 2-amino-4-chloro-6-phenyl-pyrimidine-5-carbonitrile as a light yellow crystalline solid. EI-MS m/e (%): 232 (M{37Cl}+, 26), 230 (M{35Cl}+, 80), 190 ([M—Cl]+, 100), 153 (38).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customremained around 10° C
  4. filtrationThe resulting crystals were collected by filtration

出典と根拠

ORDレコード
ord-89ba58687bbc40b4a187049a1e264642
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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