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

HRID 1295466

反応式

HRID 1295466 の反応式
[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]

参加物

6

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2 回HCID 744692,5-Dimethoxyphenylacetic acidHCID 858276526-Chloro-5-amino-4-butyl pyrimidine

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b1e0425e34e94f4fa688641bbb444d19
出典データセット
uspto-grants-2007_07
特許番号
US07241890B2

関連ノート

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