2-Propanesulfonyl chloride → Propane-2-sulfonic acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-yl ester

HRID 48458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 48458
CC([O-])(C)C.[K+].[NH2:7][C:8]1[N:13]=[C:12]([NH2:14])[C:11]([CH2:15][C:16]2[CH:17]=[C:18]([OH:26])[C:19]3[CH:20]=[CH:21][N:22]([CH3:25])[C:23]=3[CH:24]=2)=[CH:10][N:9]=1.[CH3:27][CH:28]([S:30](Cl)(=[O:32])=[O:31])[CH3:29]>CN(C)C=O>[NH2:7][C:8]1[N:13]=[C:12]([NH2:14])[C:11]([CH2:15][C:16]2[CH:24]=[C:23]3[C:19]([CH:20]=[CH:21][N:22]3[CH3:25])=[C:18]([O:26][S:30]([CH:28]([CH3:29])[CH3:27])(=[O:32])=[O:31])[CH:17]=2)=[CH:10][N:9]=1

Komponenten

5

Edukt 3

HCID 824082-Propanesulfonyl chlorideHCID 227428906-(2,4-Diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-olHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 86759375Propane-2-sulfonic acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-yl esterAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium tert-butylate (150 mg, 1.31 mmol) was added at 0° C. (ice bath) to a solution of 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-ol (Example 4; 293 mg, 1.09 mmol) in N,N-dimethylformamide (33 mL). After 30 min the solution was treated with propane-2-sulfonyl chloride (190 mg, 1.31 mmol), and the ice bath was removed. After 2.5 h the reaction mixture was poured into ice water, set to pH 9-10 with 25% aqueous ammonia solution, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried (MgSO4), and evaporated. Column chromatography (SiO2; CH2Cl2/MeOH/NH4OH19:1:0.05) afforded the title compound (153 mg, 37%). White solid.

Aufarbeitung

  1. customthe ice bath was removed
  2. additionAfter 2.5 h the reaction mixture was poured into ice water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f70a69f9a0aa4bd8a59d473235e658e6
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703397B2

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