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

HRID 1295466

Reaktionsgleichung

Reaktionsgleichung von HRID 1295466
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b1e0425e34e94f4fa688641bbb444d19
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241890B2

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