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

HRID 1095474

반응식

HRID 1095474 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 4-chloro-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine (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-38c2c6bee409438a983fc8b47af8e9e3
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138194B2

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