p-Toluenesulfonic acid → 6-chloro-8-(2,5-dimethoxybenzyl)-N9-butyl purine

HRID 1295467

반응식

HRID 1295467 반응식
[CH2:1]([NH:5][C:6]1[C:11]([NH:12][C:13](=O)[CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[O:23][CH3:24])=[C:10]([Cl:26])[N:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:26][C:10]1[N:9]=[CH:8][N:7]=[C:6]2[C:11]=1[N:12]=[C:13]([CH2:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=1[O:23][CH3:24])[N:5]2[CH2:1][CH2:2][CH2:3][CH3:4]

참가 물질

4

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 11660875N-(4-butylamino-6-chloro-pyrimidin-5-yl)-2-(2,5-dimethoxyphenyl)acetamide

생성물 1

HCID 858276576-chloro-8-(2,5-dimethoxybenzyl)-N9-butyl purine

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of N-(4-butylamino-6-chloro-pyrimidin-5-yl)-2-(2,5-dimethoxyphenyl) acetamide (1 mmol) and p-TSA (0.5 mmol) in toluene was refluxed for 72 h. Solvent was removed, diluted with EtOAc and washed with water, bicarbonate and dried. Purification on a silica gel column (200-400 mesh, Fisher Scientific, Tustin, Calif., USA) gave 6-chloro-8-(2,5-dimethoxybenzyl)-N9-butyl purine. Rf=0.65 in 1:1 EtOAc:hexane. 1H NMR (DMSO-d6) δ 8.7 (s, 1H), 6.96 (d, 1H), 6.84 (m, 1H), 6.8 (dd, 1H), 4.28 (s, 2H), 4.23 (t, 2H), 3.69 (s, 3H), 3.67 (s, 3H), 1.62 (m, 2H), 1.25 (m, 2H), 0.88 (t, 3H).

후처리

  1. temperaturewas refluxed for 72 h
  2. customSolvent was removed
  3. additiondiluted with EtOAc
  4. washwashed with water, bicarbonate
  5. customdried
  6. customPurification on a silica gel column (200-400 mesh, Fisher Scientific, Tustin, Calif., USA)

출처 및 근거

ORD 기록
ord-867b123fb1914c5d8e5db6b8d90fc0cb
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241890B2

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