4-Toluenesulfonyl chloride → 6-benzyl-4-methoxy-2-(5-methyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80795

Reaktionsgleichung

Reaktionsgleichung von HRID 80795
[CH2:1]([N:8]1[CH2:29][CH2:28][C:11]2[N:12]=[C:13]([C:18]3[C:26]([CH3:27])=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[N:21][NH:22]4)[N:14]=[C:15]([O:16][CH3:17])[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[S:32](Cl)([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33].[NH4+].[Cl-]>C1COCC1>[CH2:1]([N:8]1[CH2:29][CH2:28][C:11]2[N:12]=[C:13]([C:18]3[C:26]([CH3:27])=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[N:21][N:22]4[S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[N:14]=[C:15]([O:16][CH3:17])[C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 712404666-benzyl-4-methoxy-2-(5-methyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Produkt 1

HCID 712406006-benzyl-4-methoxy-2-(5-methyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-Benzyl-4-methoxy-2-(5-methyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (2.00 g, 5.19 mmol) was added to a suspension of NaH (60% dispersion in mineral oil, 415 mg, 10.4 mmol) in THF (50 mL) at 0° C. After 20 min, TsCl (1.19 g, 6.23 mmol) was added. The reaction mixture was stirred for 20 min and sat aq NH4Cl solution was added to quench excess base. The resulting mixture was extracted with EtOAc (3×). The combined organics were dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc/heptane) to provide 6-benzyl-4-methoxy-2-(5-methyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 540.2 (M+H)+.

Aufarbeitung

  1. additionwas added
  2. customto quench excess base
  3. extractionThe resulting mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-100% EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-e2c84dd44598474ca072f91e0a3b2326
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846656B2

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