Water → 7-Benzyl-8-(3-(1,3-dithian-2-ylidene)-cyclopentyl)-1,3-dipropylpurine-2,6-dione

HRID 1684522노트

반응식

HRID 1684522 반응식
C([Li])CCC.C[Si](C)(C)[CH:8]1[S:13][CH2:12][CH2:11][CH2:10][S:9]1.[CH2:16]([N:23]1[C:31]2[C:30](=[O:32])[N:29]([CH2:33][CH2:34][CH3:35])[C:28](=[O:36])[N:27]([CH2:37][CH2:38][CH3:39])[C:26]=2[N:25]=[C:24]1[CH:40]1[CH2:44][CH2:43][C:42](=O)[CH2:41]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CCCCCC.O1CCCC1>[CH2:16]([N:23]1[C:31]2[C:30](=[O:32])[N:29]([CH2:33][CH2:34][CH3:35])[C:28](=[O:36])[N:27]([CH2:37][CH2:38][CH3:39])[C:26]=2[N:25]=[C:24]1[CH:40]1[CH2:41][CH2:42][C:43](=[C:8]2[S:13][CH2:12][CH2:11][CH2:10][S:9]2)[CH2:44]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 834132-Trimethylsilyl-1,3-dithianeHCID 149891347-Benzyl-8-(3-oxocyclopentyl)-1,3-dipropylpurine-2,6-dioneHCID 178418339Butyllithium

생성물 1

HCID 190398217-Benzyl-8-(3-(1,3-dithian-2-ylidene)-cyclopentyl)-1,3-dipropylpurine-2,6-dione

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-70 °C

실험 절차

At -75° C. 14.37 ml (0.023 mol) of a 1.6M solution of butyl lithium in n-hexane is added dropwise to 4.0 g of 2-trimethylsilyl-1,3-dithiane (0.021 mol) in 15 ml of absolute tetrahydrofuran and the mixture is stirred for a further 30 minutes at -70° C. Then at the same temperature a solution of 8.0 g (0.020 mol) of 7-benzyl-8-(3-oxocyclopentyl)-1,3-dipropylpurine-2,6-dione in 70 ml of absolute tetrahydrofuran is added dropwise. The mixture is stirred for 2 hours at -70° C. and then for 2 hours at -30° C., then water is carefully added at -30° C. The phases are separated, the organic phase is evaporated down, the residue is taken up in dichloromethane, washed with water and the solution is dried and evaporated down. Purification is carried out by chromatography on silica gel using a mixture of cyclohexane/ethyl acetate as eluant in the ratio 3:1. 3.55 g (35.5% of theory) of the title compound are obtained in the form of a yellowish oil which crystallises when left to stand.

후처리

  1. customAt -75° C
  2. stirringThe mixture is stirred for 2 hours at -70° C.
  3. waitfor 2 hours at -30° C.
  4. customThe phases are separated
  5. customthe organic phase is evaporated down
  6. washwashed with water
  7. customthe solution is dried
  8. customevaporated down
  9. customPurification
  10. additiona mixture of cyclohexane/ethyl acetate as eluant in the ratio 3:1

출처 및 근거

ORD 기록
ord-e895dd3aaf744267b851878c7d1b172b
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05641784

반응 노트

불러오는 중…