Ethyl isothiocyanatoformate → Ethyl (5-chlorothiazolo[5,4-d]pyrimidin-2-yl)carbamate

HRID 1875971ノート

反応式

HRID 1875971 の反応式
[CH2:1]([O:3][C:4]([N:6]=[C:7]=[S:8])=[O:5])[CH3:2].[Cl:9][C:10]1[N:15]=[C:14](Cl)[C:13]([NH2:17])=[CH:12][N:11]=1>CO>[Cl:9][C:10]1[N:11]=[CH:12][C:13]2[N:17]=[C:7]([NH:6][C:4](=[O:5])[O:3][CH2:1][CH3:2])[S:8][C:14]=2[N:15]=1

参加物

4

反応物 2

HCID 85320Ethyl isothiocyanatoformateHCID 2577975-Amino-2,4-dichloropyrimidine

生成物 1

HCID 57476592Ethyl (5-chlorothiazolo[5,4-d]pyrimidin-2-yl)carbamate収率 80.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Ethoxycarbonyl isothiocyanate (4.32 mL, 36.6 mmol) and 2,4-dichloro-pyrimidin-5-ylamine (3.00 g, 18.29 mmol) were mixed neat and sonicated for 5 minutes to help dissolve. The mixture was stirred at ambient temperature for 10 minutes, at which time the entire mixture had solidified. Methanol (100 mL) was added and the mixture was refluxed for 30 minutes, cooled to ambient temperature and the solids were collected by filtration to afford ethyl 5-chlorothiazolo[5,4-d]pyrimidin-2-ylcarbamate (3.8 g, 80% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.64 (s, 1H) 9.05 (s, 1H) 4.31 (q, J=7.19 Hz, 2H) 1.32 (t, J=7.15 Hz, 3H).

後処理

  1. customsonicated for 5 minutes
  2. dissolutionto help dissolve
  3. temperaturethe mixture was refluxed for 30 minutes
  4. temperaturecooled to ambient temperature
  5. filtrationthe solids were collected by filtration

出典と根拠

ORDレコード
ord-97a8884217814f86add29c88f61e6025
出典データセット
uspto-grants-2012_11
特許番号
US08309577B2

反応ノート

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