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

HRID 391706Notes

Reaction equation

HRID 391706 reaction equation
[NH2:1][C:2]1[C:3]([C:29](OCC)=[O:30])=[N:4][C:5]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=2)=[N:6][C:7]=1[NH:8][CH:9]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1.[NH2:34]C1C(C(OCC)=O)=NC(Cl)=NC=1NC1CCN(C(OC(C)(C)C)=O)CC1.[OH:61][C:62]1C=C(B(O)O)C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C(OC)=CC=CC=2OC)CCCCC1>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[OH:28][C:24]1[CH:23]=[C:22]([C:5]2[N:6]=[C:7]3[C:2]([NH:1][C:62](=[O:61])[N:8]3[CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[C:3]([C:29]([NH2:34])=[O:30])[N:4]=2)[CH:27]=[CH:26][CH:25]=1

Participants

9

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 57474834Ethyl 5-amino-6-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)-2-chloropyrimidine-4-carboxylateHCID 57474835Dicyclohexyl(2,6-dimethoxyphenyl)phosphineHCID 57474837Ethyl 5-amino-6-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)-2-(3-hydroxyphenyl)pyrimidine-4-carboxylate

Product 1

HCID 574748382-(3-Hydroxyphenyl)-8-oxo-9-(piperidin-4-YL)-8,9-dihydro-7H-purine-6-carboxamideYield 40%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-amino-6-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)-2-(3-hydroxyphenyl)pyrimidine-4-carboxylate. Ethyl 5-amino-6-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)-2-chloropyrimidine-4-carboxylate. (0.400 g, 1.00 mmol) 3-hydroxyphenyl boronic acid (0.207 g, 1.5 mmol), palladium(II)acetate (0.034 g, 0.15 mmol), potassium phosphate (0.430 g, 2.0 mmol) and dicyclohexyl(2,6-dimethoxyphenyl)phosphine (0.062 g, 0.15 mmol) were combined in tetrahydrofuran (6 mL) and water (0.6 ml) and reacted in the microwave at 120° C. for 30 min. The reaction was monitored via thin layer chromatography for consumption of starting materials. The solution was filtered and concentrated and the residue purified via Biotage chromatography (0-60% EtOAc in hexanes) to afford the title compound (0.120 g, 40%). MS (ESI) m/z 458.5 [M+1]+.

Workup

  1. customThe reaction was monitored via thin layer chromatography for consumption of starting materials
  2. filtrationThe solution was filtered
  3. concentrationconcentrated
  4. customthe residue purified via Biotage chromatography (0-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-85a1146afc304f83999b303d1e5e3e61
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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