3,4-dihydro-2H-pyran → 2,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

HRID 249795

반응식

HRID 249795 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.CC1(C)[C@]2(CS(O)(=O)=O)C(C[C@H]1CC2)=O>ClCCCl.C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)=[C:4]([Cl:11])[N:3]=1

참가 물질

6

반응물 3

HCID 80803,4-dihydro-2H-pyranHCID 65617D-Camphorsulfonic AcidHCID 53244122,6-Dichloropurine

생성물 1

HCID 2702652,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6212Chloroform용매

반응 조건

온도
83 °C

실험 절차

A suspension of 2,6-dichloropurine (22.0 g, 116.4 mmol), dihydropyran (11.5 mL, 126 mmol) and D-(+)-10-camphorsulfonic acid (2.20 g, 9.47 mmol) in 1,2-dichloroethane (300 mL) was stirred at 83° C. for 16 hours. The initially white suspension, after 2 hrs, turned yellow and then black. The reaction mixture was diluted with CCl3H and then washed with brine. The organic layer is dried over MgSO4, filtered, concentrated and triturated with hexane 3 times to give the desired product. 1HNMR (300 MHz, CCl3D): δ 8.33 (s, 1H), 5.75 (dd, J=10.4 Hz, 2.5 Hz, 1H), 4.18 (m, 2H), 3.79 (m, 2H), 1.84 (m, 4H).

후처리

  1. waitThe initially white suspension, after 2 hrs
  2. washwashed with brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customtriturated with hexane 3 times

출처 및 근거

ORD 기록
ord-6621c962023f47de9655ad5bd540ffe3
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863285B2

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