Ethanol → 2-(4-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 2427966ノート

反応式

HRID 2427966 の反応式
[NH2:1][C:2]1[C:3]([C:25](OCC)=[O:26])=[N:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[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].OC1C=CC([NH:37]C2N=C(C(OCC)=O)C([N+]([O-])=O)=C(NC3C=CC=CC=3OC)N=2)=CC=1.[CH2:61]([OH:63])C>[Pd]>[OH:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:5]2[N:6]=[C:7]3[C:2]([NH:1][C:61](=[O:63])[N:8]3[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:3]([C:25]([NH2:37])=[O:26])[N:4]=2)=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 702EthanolHCID 57474609Ethyl 2-(4-hydroxyphenylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 57474610Ethyl 5-amino-2-(4-hydroxyphenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate

生成物 1

HCID 249379902-(4-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide収率 98%

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

Ethyl 5-amino-2-(4-hydroxyphenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. Ethyl 2-(4-hydroxyphenylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (220 mg, 0.517 mmol) was dissolved in ethanol (10 mL) and 10% palladium on carbon (55 mg, 0.052 mmol) was added. The reaction mixture was stirred at room temperature under an atmosphere of hydrogen overnight. The reaction was then filtered through Celite, solvent was removed under reduced pressure and purified by column chromatography (60-100% ethyl acetate in hexanes). Fractions containing product were combined and the solvent evaporated to provide the title compound (201.3 mg, 0.509 mmol, 98% yield). MS (ESI) m/z 396.2 [M+1]+.

後処理

  1. filtrationThe reaction was then filtered through Celite, solvent
  2. customwas removed under reduced pressure
  3. custompurified by column chromatography (60-100% ethyl acetate in hexanes)
  4. additionFractions containing product
  5. customthe solvent evaporated

出典と根拠

ORDレコード
ord-5a5e94faebfc47849c0b91b5eb33211a
出典データセット
uspto-grants-2011_06
特許番号
US07968556B2

反応ノート

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