1,1'-Carbonyldiimidazole → 2-(2-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 391641ノート

反応式

HRID 391641 の反応式
[Si]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[N:24]=[C:23]2[C:19]([NH:20][C:21](=[O:33])[N:22]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])=[C:18]([C:34]([O:36]CC)=O)[N:17]=1)(C(C)(C)C)(C)C.[NH2:39]C1C(C(OCC)=O)=NC(NC2C=CC=CC=2O[Si](C(C)(C)C)(C)C)=NC=1NC1C=CC=CC=1OC.C(N1C=CN=C1)(N1C=CN=C1)=O>C(Cl)Cl>[OH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[N:24]=[C:23]2[C:19]([NH:20][C:21](=[O:33])[N:22]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])=[C:18]([C:34]([NH2:39])=[O:36])[N:17]=1

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 57474634Ethyl 5-amino-2-(2-(tert-butyldimethylsilyloxy)phenyl amino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylateHCID 57474635Ethyl 2-(2-(tert-butyldimethylsilyloxy)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate

生成物 1

HCID 249381082-(2-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide収率 96%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Ethyl 2-(2-(tert-butyldimethylsilyloxy)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate. Ethyl 5-amino-2-(2-(tert-butyldimethylsilyloxy)phenyl amino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate (232.6 mg, 0.456 mmol) was dissolved in methylene chloride (5 mL) and 1,1′-carbonyldiimidazole (740 mg, 4.56 mmol) was added. The reaction was refluxed for 1H and then stirred at room temperature overnight. Solvent was removed under reduced pressure and crude was purified by column chromatography (50% ethyl acetate in hexanes). Fractions containing product were combined and the solvent evaporated to provide the title compound (235.2 mg, 0.439 mmol, 96% yield) as a yellow solid. MS (ESI) m/z 536.4 [M+1]+.

後処理

  1. temperatureThe reaction was refluxed for 1H
  2. customSolvent was removed under reduced pressure and crude
  3. customwas purified by column chromatography (50% ethyl acetate in hexanes)
  4. additionFractions containing product
  5. customthe solvent evaporated

出典と根拠

ORDレコード
ord-eb8676e3539142b999a1da582eaca39f
出典データセット
uspto-grants-2013_02
特許番号
US08383634B2

反応ノート

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