Ammonia → HCID 25133005, Verbindung

HRID 1042275

Reaktionsgleichung

Reaktionsgleichung von HRID 1042275
F[C:2]1[C:7]([C:8]2[C:9]3[CH:16]=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:17][C:18]1[C:19]([CH3:37])=[CH:20][CH:21]=[C:22]2[C:27]=1[N:26]=[CH:25][N:24]=[C:23]2[NH:28][C:29]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].N>C1COCC1.CO.CC(O)=O>[N:11]1[C:10]2[NH:14][CH:15]=[CH:16][C:9]=2[C:8]([C:7]2[C:2]([NH:17][C:18]3[C:19]([CH3:37])=[CH:20][CH:21]=[C:22]4[C:27]=3[N:26]=[CH:25][N:24]=[C:23]4[NH:28][C:29]3[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)=[N:13][CH:12]=1

Komponenten

8

Edukt 4

HCID 222AmmoniaHCID 2733832Lithium HexamethyldisilazideHCID 596273704-(2-fluoropyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidineHCID 68725343HCID 68725343, Verbindung

Produkt 1

HCID 25133005HCID 25133005, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 4-(2-fluoropyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine (78 mg, 363 μmol) and 4-(8-amino-7-methylquinazolin-4-ylamino)benzonitrile (100 mg, 363 μmol) in THF (4 mL) was sonicated until all solids became a fine powder. Lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran; 1.64 mL, 1.64 mmol) was then added dropwise with stirring (all solids dissolved and then some solid appeared again). The mixture was stirred at rt for 10 min and then heated in a microwave at 120° C. for 30 min. The mixture was poured into MeOH (10 mL) and AcOH (0.5 mL) and stirred for 10 min, then 2 M NH3 in MeOH (20 mL) was added. Solvent was removed under vacuum and the residue was purified by flash chromatography eluting with MeOH(NH3)/DCM to give 4-(8-(3-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile. MS (ESI, pos. ion) m/z: 470.2 [M+H]+

Aufarbeitung

  1. customwas sonicated until all solids
  2. dissolutiondissolved
  3. stirringThe mixture was stirred at rt for 10 min
  4. stirringstirred for 10 min
  5. customSolvent was removed under vacuum
  6. customthe residue was purified by flash chromatography
  7. washeluting with MeOH(NH3)/DCM

Quellen und Nachweise

ORD-Eintrag
ord-6dea8a3f083f4893bea6ef05cc91325e
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557830B2

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