Hydrogen Bromide → trans-6,7-Dichloro-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]thieno[3,2-d]pyrimidin-4(3H)-one Dihydrobromide

HRID 4270노트

반응식

HRID 4270 반응식
[Cl:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][C:13](=[O:26])[CH2:14][C@H:15]3[C@H:20]([OH:21])[CH2:19][CH2:18][CH2:17][N:16]3C(OC)=O)[CH:6]=[N:5][C:4]=2[C:3]=1[Cl:27].[BrH:28]>C(O)C>[BrH:28].[BrH:28].[Cl:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][C:13](=[O:26])[CH2:14][C@H:15]3[C@H:20]([OH:21])[CH2:19][CH2:18][CH2:17][NH:16]3)[CH:6]=[N:5][C:4]=2[C:3]=1[Cl:27]

참가 물질

4

반응물 2

HCID 260Hydrogen BromideHCID 70393530Methyl trans-2-[3-(6,7-Dichloro-3,4-dihydro-4-oxothieno[3,2-d]pyrimidin-3-yl)-2-oxopropyl]-3-hydroxy-1-piperidinecarboxylate

생성물 1

HCID 70417958trans-6,7-Dichloro-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]thieno[3,2-d]pyrimidin-4(3H)-one Dihydrobromide

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

In a 15 ml single-neck round bottom flask equipped with a reflux condenser, a solution of 0.190 g (0.00044 mole) of methyl trans-2-[3-(6,7-dichloro-3,4-dihydro-4-oxothieno[3,2-d]pyrimidin-3-yl)-2-oxopropyl]-3-hydroxy-1-piperidinecarboxylate and 6.2 ml of 48% aqueous hydrobromic acid was immersed in an oil bath preheated to 150° C. Heating was continued for three minutes. The solution was allowed to cool to room temperature, and the volatile components were evaporated under reduced pressure. Ethanol (5 ml) was added to the residue, and again the mixture was evaporated to dryness. This operation was repeated once more to afford a dark residue which was then taken up in 3 ml of ethanol. After standing overnight at room temperature, the solution was diluted with 1 ml of ethanol and then heated at reflux briefly. Upon cooling a greyish solid precipitated. The mother liquor was removed by means of a pipette, and the residue was dried in a vacuum oven at 55° C. for 45 minutes to furnish the title compound: yield 0.080 g (48%); mass spectrum peaks at 357 (molecular ion - 18), 155, 137 (parent peak) amongst others; 1H-nmr (CF3CO2H) delta 1.3-2.0 ppm (multiplet, 4H, OCHCH2CH2CH2N), 2.8-3.4 (multiplet, 6H, COCH2CH, NCH2, NCHCH2, CHOH), 3.7 (singlet, 1H, OH), 4.9 (singlet 2H, NCH2CO), 8.3 (broad singlet, 1H, N=CH--N).

후처리

  1. customIn a 15 ml single-neck round bottom flask equipped with a reflux condenser
  2. custompreheated to 150° C
  3. temperatureHeating
  4. customthe volatile components were evaporated under reduced pressure
  5. additionEthanol (5 ml) was added to the residue
  6. customagain the mixture was evaporated to dryness
  7. customto afford a dark residue which
  8. waitAfter standing overnight at room temperature
  9. temperatureheated
  10. temperatureat reflux briefly
  11. temperatureUpon cooling a greyish solid
  12. customprecipitated
  13. customThe mother liquor was removed by means of a pipette
  14. customthe residue was dried in a vacuum oven at 55° C. for 45 minutes

출처 및 근거

ORD 기록
ord-303909f3f84f4a05bac9039b7243a17c
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725599

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