4-Toluenesulfonyl chloride → N-(4-butylamino-6-chloro-pyrimidin-5-yl)-2-(2,5-dimethoxyphenyl)acetamide

HRID 1295466

반응식

HRID 1295466 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][C:12]([OH:14])=O.CC[N:17](CC)CC.[C:22]1([CH3:32])[CH:27]=[CH:26]C(S(Cl)(=O)=O)=CC=1.[Cl:33][C:34]1[N:39]=[CH:38][N:37]=[C:36](CCCC)[C:35]=1[NH2:44]>C(Cl)Cl>[CH2:26]([NH:17][C:36]1[C:35]([NH:44][C:12](=[O:14])[CH2:11][C:4]2[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[C:34]([Cl:33])[N:39]=[CH:38][N:37]=1)[CH2:27][CH2:22][CH3:32]

참가 물질

6

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2회HCID 744692,5-Dimethoxyphenylacetic acidHCID 858276526-Chloro-5-amino-4-butyl pyrimidine

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2,5-dimethoxyphenylacetic acid (1 mmol) and Et3N (1 mmol) in CH2Cl2 was added p-toluenesulfonyl chloride (1 mmol) at rt. After 1 h, the mixture was treated with a solution of the product of step 1, 6-chloro-5-amino-4-butyl pyrimidine (1 mmol in CH2Cl2), followed by addition of Et3N (2 mmol). The resultant mixture was refluxed for 20 h. Solvent was removed and the residue dissolved into EtOAc, the organic layer washed with water and dried. The crude compound was taken into acetone, and precipitated product filtered out and washed with a small amount of acetone to give N-(4-butylamino-6-chloro-pyrimidin-5-yl)-2-(2,5-dimethoxyphenyl) acetamide. Rf=0.45 in 1:1 EtOAc:hexane. 1H NMR (DMSO-d6) δ 9.37 (s, 1H), 8.17 (s, 1H), 7.11 (t, 1H), 6.9 (d, 1H), 6.88 (d, 1H), 6.78 (dd, 1H), 3.73 (s, 3H), 3.69 (s, 3H), 3.63 (s, 3H), 3.35 (m, 2H), 1.48 (m, 2H), 1.29 (m, 2H), 0.88 (t, 3H).

후처리

  1. customSolvent was removed
  2. dissolutionthe residue dissolved into EtOAc
  3. washthe organic layer washed with water
  4. customdried
  5. customprecipitated product
  6. filtrationfiltered out
  7. washwashed with a small amount of acetone

출처 및 근거

ORD 기록
ord-b1e0425e34e94f4fa688641bbb444d19
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241890B2

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