Potassium Phosphate, Tribasic → 2-(3-Hydroxyphenyl)-9-(1H-indol-4-YL)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 391696ノート

反応式

HRID 391696 の反応式
[NH2:1][C:2]1[C:3]([C:34](OC)=[O:35])=[N:4][C:5]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=2)=[N:6][C:7]=1[NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2S(C1C=CC=CC=1)(=O)=O.[NH2:38]C1C(C(OC)=O)=NC(Cl)=NC=1NC1C=CC=C2C=1C=CN2S(C1C=CC=CC=1)(=O)=O.[OH:69][C:70]1C=C(B(O)O)C=CC=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:33][C:29]1[CH:28]=[C:27]([C:5]2[N:6]=[C:7]3[C:2]([NH:1][C:70](=[O:69])[N:8]3[C:9]3[CH:17]=[CH:16][CH:15]=[C:14]4[C:10]=3[CH:11]=[CH:12][NH:13]4)=[C:3]([C:34]([NH2:38])=[O:35])[N:4]=2)[CH:32]=[CH:31][CH:30]=1

参加物

8

反応物 5

HCID 62657Potassium Phosphate, TribasicHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57474791Methyl 5-amino-2-(3-hydroxyphenyl)-6-(1-(phenylsulfonyl)-1H-indol-4-ylamino)pyrimidine-4-carboxylateHCID 86627729Methyl 5-amino-2-chloro-6-(1-(phenylsulfonyl)-1H-indol-4-ylamino)pyrimidine-4-carboxylate

生成物 1

HCID 574747952-(3-Hydroxyphenyl)-9-(1H-indol-4-YL)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide収率 28%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8857Ethyl Acetate溶媒

実験手順

Methyl 5-amino-2-(3-hydroxyphenyl)-6-(1-(phenylsulfonyl)-1H-indol-4-ylamino)pyrimidine-4-carboxylate. Methyl 5-amino-2-chloro-6-(1-(phenylsulfonyl)-1H-indol-4-ylamino)pyrimidine-4-carboxylate (0.31 g, 0.68 mmol), 3-hydroxyphenyboronic acid (0.14 g, 1.0 mmol), palladium (II) acetate (30 mg, 0.14 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (60 mg, 0.14 mmol), and potassium phosphate (0.36 g, 2.1 mmol) were reacted together according to General Procedure E. The reaction was diluted with EtOAc (40 mL) and washed with 5% HCl (aq, 40 mL). The organic layer was separated, dried over sodium sulfate, filtered, and concentrated. The crude residue was subjected to silica gel chromatography (50% Hexanes in EtOAc). Concentration of the desired fractions afforded the title compound (0.1 g, 0.19 mmol, 28%). MS (ESI) m/z 516.3[M+1]+.

後処理

  1. washwashed with 5% HCl (aq, 40 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-d47a6365503b465b94d015a66a3bcc76
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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