Phosphorus oxychloride → 3-Chloro-8-thia-4,6-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2,4,6-tetraene

HRID 1891025

반응식

HRID 1891025 반응식
[N:1]1[C:6]2[S:7][C:8]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[C:5]=2[C:4](=O)[NH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:17].C(=O)(O)[O-].[Na+]>O>[Cl:17][C:4]1[C:5]2[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:8]=3[S:7][C:6]=2[N:1]=[CH:2][N:3]=1

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 986145,6,7,8-Tetrahydro(1)benzothieno(2,3-D)pyrimidin-4(3H)-oneHCID 516892Sodium Bicarbonate

생성물 1

HCID 6995153-Chloro-8-thia-4,6-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2,4,6-tetraene수율 60%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

A mixture of 3,4,5,6,7,8-hexahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-one (0.8 g) and POCl3 (10 mL) was heated at 55-65° C. for 3 h. Water was then added followed by sodium bicarbonate. The resulting mixture was extracted with ethyl acetate. The organic layer was concentrated and the crude compound was purified by silica gel column chromatography using a mixture of hexanes:ethyl acetate (20:1), to give the title compound (0.52 g, 60%). 1H NMR (300 MHz, CDCl3): δ 8.69 (s, 1H), 3.10-3.07 (m, 2H), 2.88-2.86 (m, 2H), 1.89-1.92 (m, 4H). LC-MS (ESI) m/z 225.3 (M+H).

후처리

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. customthe crude compound was purified by silica gel column chromatography
  4. additiona mixture of hexanes:ethyl acetate (20:1)

출처 및 근거

ORD 기록
ord-9787b7ab0295430cbdbb8cfbeb2a57b7
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507502B2

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