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

HRID 391696노트

반응식

HRID 391696 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8857Ethyl Acetate용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-d47a6365503b465b94d015a66a3bcc76
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383634B2

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