Hydrochloric Acid → HCID 178494908, Verbindung

HRID 1723656

Reaktionsgleichung

Reaktionsgleichung von HRID 1723656
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([CH3:13])=[N:10][C:9]=2[CH:14]([CH3:18])[CH2:15][O:16][CH3:17])[CH:5]=[CH:4][N:3]=1.[O:19]1[CH2:23][CH2:22][CH2:21][CH:20]1[CH2:24][NH:25][S:26]([C:29]1[CH:34]=[CH:33][C:32](I)=[CH:31][CH:30]=1)(=[O:28])=[O:27].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].Cl.CCOCC>O1CCOCC1.CO.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[CH3:17][O:16][CH2:15][CH:14]([C:9]1[N:10]=[C:11]([CH3:13])[NH:12][C:8]=1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:32]2[CH:33]=[CH:34][C:29]([S:26](=[O:27])(=[O:28])[NH:25][CH2:24][CH:20]3[CH2:21][CH2:22][CH2:23][O:19]3)=[CH:30][CH:31]=2)[N:7]=1)[CH3:18]

Komponenten

10

Edukt 6

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 634876Binap, (A+-)-HCID 29000714-iodo-N-(tetrahydro-2-furanylmethyl)benzenesulfonamideHCID 23676156Sodium t-butoxideHCID 178494909HCID 178494909, Verbindung

Produkt 1

HCID 178494908HCID 178494908, VerbindungAusbeute 31,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9832798Tris(dibenzylideneacetone) dipalladiumKatalysatorHCID 887MethanolLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 2-amino-4-(1-methoxyprop-2-yl-2-methylimidazol-5-yl)pyrimidine (Method 53; 118 mg, 0.75 mmol), N-(tetrahydrofur-2-ylmethyl)4-iodobenzenesulphonamide (Method 68; 413 mg, 1.13 mmol), tris(dibenzylideneacetone) dipalladium (0) (35 mg, 0.038 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (47 mg, 0.076 mmol) in dioxane (10 mL) was added sodium t-butoxide (258 mg, 2.69 mmol) and the mixture heated at 80° C. overnight. The reaction was cooled to room temperature and MeOH (5 ml) was added and the mixture poured onto an Isolute SCX-2 column, eluted first with MeOH (10×30 ml) and the product was then eluted with 10% methanolic ammonia (10×30 ml). The solvent was removed by evaporation and the residue purified by flash chromatography on silica gel eluting with DCM/MeOH (100:0 increasing in polarity to 97:3) to yield a foam which was dissolved in MeOH (2 ml) and treated with 1M HCl in ether (300 μL, 0.30 mmol) for 5 minutes. Solvent was evaporated in vacuo to yield a yellow solid (115 mg, 30%). NMR: 1.52 (d, 3H), 1.75 (m, 4H), 2.70 (m, 2H), 2.79 (s, 3H); 3.16 (s, 3H), 3.63 (m, 5H), 5.65 (m, 1H), 7.25 (d, 1H), 7.56 (t, 1H), 7.70 (d, 2H), 7.88 (d, 2H), 8.21 (s, 1H), 8.68 (d, 1H), 10.19 (brs, 1H); m/z 487.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. additionthe mixture poured onto an Isolute SCX-2 column
  3. washeluted first with MeOH (10×30 ml)
  4. washthe product was then eluted with 10% methanolic ammonia (10×30 ml)
  5. customThe solvent was removed by evaporation
  6. customthe residue purified by flash chromatography on silica gel eluting with DCM/MeOH (100:0 increasing in polarity to 97:3)
  7. customto yield a foam which
  8. customSolvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9ba575812f664c8cbe1106d686ae5eac
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485638B2

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