Imidazole → 2-(2-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 391640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391640
[NH2:1][C:2]1[C:3]([C:32](OCC)=[O:33])=[N:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][Si](C(C)(C)C)(C)C)=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16].NC1C(C(OCC)=O)=NC(NC2C=CC=CC=2O)=NC=1NC1C=CC=C[C:46]=1[O:51]C.[Si](Cl)(C(C)(C)C)(C)C.[NH:74]1C=CN=C1>C(Cl)Cl>[OH:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:5]1[N:6]=[C:7]2[C:2]([NH:1][C:46](=[O:51])[N:8]2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:3]([C:32]([NH2:74])=[O:33])[N:4]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57474631Ethyl 5-amino-2-(2-hydroxyphenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylateHCID 57474634Ethyl 5-amino-2-(2-(tert-butyldimethylsilyloxy)phenyl amino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate

Produkt 1

HCID 249381082-(2-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamideAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ethyl 5-amino-2-(2-(tert-butyldimethylsilyloxy)phenylamino)-6-(2-methoxyphenyl amino)pyrimidine-4-carboxylate. Ethyl 5-amino-2-(2-hydroxyphenylamino)-6-(2-methoxy phenylamino)pyrimidine-4-carboxylate (184 mg, 0.465 mmol) was dissolved in methylene chloride (5 mL) and tert-butyldimethylsilyl chloride (77 mg, 0.512 mmol) and imidazole (38.0 mg, 0.558 mmol) were added. The reaction mixture was stirred overnight at room temperature. Solvent was removed under reduced pressure and crude was purified by column chromatography (20% ethyl acetate in hexanes). Fractions containing product were combined and the solvent evaporated to provide the title compound (232.6 mg, 0.456 mmol, 98% yield) as a yellow solid. MS (ESI) m/z 510.5 [M+1]+.

Aufarbeitung

  1. customSolvent was removed under reduced pressure and crude
  2. customwas purified by column chromatography (20% ethyl acetate in hexanes)
  3. additionFractions containing product
  4. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-56b160d05c1e4342adb97f140d24a397
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383634B2

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