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Sodium hydride → 4,4-dimethyl-3-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-{4-[(trifluoromethyl)sulfanyl]phenyl}tetrahydropyrimidin-2(1H)-one

HRID 711300
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 711300
[CH3:1][C:2]1([CH3:20])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)[C:4](=[O:19])[NH:3]1.[H-].[Na+].Cl[CH2:24][C:25]1[C:33]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[N:27](C(OC(C)(C)C)=O)[CH:26]=1>CN(C=O)C>[CH3:1][C:2]1([CH3:20])[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14][C:15]([F:18])([F:17])[F:16])=[CH:12][CH:13]=2)[C:4](=[O:19])[N:3]1[CH2:24][C:25]1[C:33]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 21463021tert-Butyl 3-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylateHCID 1180733344,4-dimethyl-1-{4-[(trifluoromethyl) sulfanyl]phenyl}tetrahydropyrimidin-2(1H)-one

Produkt 1

HCID 722044234,4-dimethyl-3-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-{4-[(trifluoromethyl)sulfanyl]phenyl}tetrahydropyrimidin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of the 4,4-dimethyl-1-{4-[(trifluoromethyl) sulfanyl]phenyl}tetrahydropyrimidin-2(1H)-one (10 mg, 0.03 mmol) in 2 mL DMF was added NaH (2.4 mg, 0.03 mmol). The mixture was allowed to stir at ambient temperature for 10 min. The reaction was treated with tert-butyl 3-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (8.8 mg, 0.03 mmol) and allowed to stir at ambient temperature for 16 h. The reaction was partitioned between water and ether. The organics were washed with water and brine, then dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography to give 4,4-dimethyl-3-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-{4-[(trifluoromethyl)sulfanyl]phenyl}tetrahydropyrimidin-2(1H)-one. 1H NMR (399 MHz, CDCl3): δ 9.05 (s, 1 H); 8.30 (d, J=4.7 Hz, 1 H); 8.11 (d, J=7.9 Hz, 1 H); 7.63 (d, J=8.2 Hz, 2 H); 7.46-7.41 (m, 2 H); 7.36 (s, 1 H); 7.11-7.06 (m, 1 H); 4.80 (s, 2 H); 3.76-3.69 (m, 2H); 2.04-1.97 (m, 2 H); 1.36 (s, 6 H). LCMS [M+H]+=435.3.

Aufarbeitung

  1. stirringto stir at ambient temperature for 16 h
  2. customThe reaction was partitioned between water and ether
  3. washThe organics were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-838931ae5d9d47ee8b15f683bf8f51c8
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181261B2

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