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

HRID 250106노트

반응식

HRID 250106 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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, 1 H) 9.05 (s, 1 H) 4.31 (q, J=7.19 Hz, 2 H) 1.32 (t, J=7.15 Hz, 3 H).

후처리

  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

출처 및 근거

ORD 기록
ord-b577a63e1316425aa9a46f784363f765
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863291B2

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