Sodium Bicarbonate → HCID 56594867, Verbindung

HRID 1038712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038712
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[N:13]=[C:14]=[O:15].[CH3:16][N:17]([CH2:19][C:20]1[CH:21]=[C:22]([NH:26][C:27]2[CH:32]=[C:31]([NH:33][CH3:34])[N:30]=[CH:29][N:28]=2)[CH:23]=[CH:24][CH:25]=1)[CH3:18].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[NH:13][C:14](=[O:15])[N:33]([C:31]1[CH:32]=[C:27]([NH:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][N:17]([CH3:16])[CH3:18])[CH:21]=2)[N:28]=[CH:29][N:30]=1)[CH3:34]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 66669947N4-[3-[(Dimethylamino)methyl]phenyl]-N6-methyl-4,6-pyrimidinediamineHCID 860869932,6-Dichloro-3,5-dimethoxyphenyl isocyanate

Produkt 1

HCID 56594867HCID 56594867, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2,6-dichloro-3,5-dimethoxyphenylisocyanate (1.25 eq.) is added to a solution of N-(3-dimethylaminomethyl-phenyl)-N′-methyl-pyrimidine-4,6-diamine (93 mg, 0.36 mmol, 1 eq.) in toluene (3 ml), at 70° C. and under an argon atmosphere. The resulting mixture is stirred at 70° C. for 18 h, allowed to cool to RT, and diluted with DCM and a saturated aqueous solution of sodium bicarbonate. The aqueous layer is separated and extracted with DCM. The organic phase is washed with brine, dried (sodium sulfate), filtered and concentrated. Purification of the crude product by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1) affords 121 mg of the title compound as a white solid: ESI-MS: 504.9/506.9 [MH]+; tR=3.64 min (purity: 100%, gradient J); TLC: Rf=0.12 (DCM/MeOH+1% NH3aq, 9:1).

Aufarbeitung

  1. temperatureto cool to RT
  2. customThe aqueous layer is separated
  3. extractionextracted with DCM
  4. washThe organic phase is washed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the crude product by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-0bdd767045b24fcda7a4f0f2212535bf
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552002B2

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