Sodium hydride → 2-chloro-4-(4-cyclopropyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidine

HRID 1516850

Reaktionsgleichung

Reaktionsgleichung von HRID 1516850
[H-].[Na+].[CH:3]1([C:6]2[CH:11]=[C:10]([CH3:12])[C:9]([OH:13])=[C:8]([CH3:14])[CH:7]=2)[CH2:5][CH2:4]1.[Cl:15][C:16]1[N:17]=[C:18](Cl)[C:19]2[NH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>CN1C(=O)CCC1.O>[Cl:15][C:16]1[N:17]=[C:18]([O:13][C:9]2[C:8]([CH3:14])=[CH:7][C:6]([CH:3]3[CH2:5][CH2:4]3)=[CH:11][C:10]=2[CH3:12])[C:19]2[NH:24][CH:23]=[CH:22][C:20]=2[N:21]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 53750532,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidineHCID 576935554-Cyclopropyl-2,6-dimethylphenol

Produkt 1

HCID 576936052-chloro-4-(4-cyclopropyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidineAusbeute 10,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Versuchsvorschrift

To a stirred suspension of NaH (25 mg, 0.64 mmol) in dry NMP (1.5 mL) was added 4-cyclopropyl-2,6-dimethylphenol (103 mg, 0.64 mmol) and the resolution mixture was stirred at room temperature for 30 min under argon. The reaction mixture was added to a solution of 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (120 mg, 0.64 mmol) in dry NMP (1.7 mL) and heated at 90° C. for 16 h. After completion of the reaction, the resulting mixture was diluted with water and washed with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (4:1-2:1), to give the product as a light yellow solid (20.2 mg, 8%).

Aufarbeitung

  1. temperatureheated at 90° C. for 16 h
  2. customAfter completion of the reaction
  3. washwashed with EtOAc
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography
  9. washeluting with hexanes/ethyl acetate (4:1-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-ccb2945576734e0688a96ea7a69e4997
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227601B2

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