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

HRID 391696Notes

Reaction equation

HRID 391696 reaction equation
[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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-d47a6365503b465b94d015a66a3bcc76
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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