Potassium Phosphate, Tribasic → HCID 57474587, compound

HRID 2427961Notes

Reaction equation

HRID 2427961 reaction equation
[NH2:1][C:2]1[C:3]([C:20]([O-:22])=O)=[N:4][C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)=[N:6][C:7]=1[NH:8][C:9]([CH3:12])([CH3:11])[CH3:10].[NH2:23]C1C(C([O-])=O)=NC(Cl)=NC=1NC(C)(C)C.[OH:39][C:40]1C=C(B(O)O)C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>O1CCCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:9]([N:8]1[C:40](=[O:39])[NH:1][C:2]2[C:7]1=[N:6][C:5]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=1)=[N:4][C:3]=2[C:20]([NH2:23])=[O:22])([CH3:11])([CH3:10])[CH3:12]

Participants

9

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57474592HCID 57474592, compoundHCID 178448858HCID 178448858, compound

Product 1

HCID 57474587HCID 57474587, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-6-tert-butylamino-2-(3-hydroxy-phenyl)-pyrimidine-4-carboxylate. In a microwave flask was placed 5-amino-6-tert-butylamino-2-chloro-pyrimidine-4-carboxylate (0.46 g, 1.69 mmol), 3-hydroxyphenylboronic acid (0.35 g, 2.53 mmol), potassium phosphate (0.72 g, 3.4 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.10 g, 0.25 mmol) and palladium (II) acetate (0.06 g, 0.25 mmol) in tetrahydrofuran (17 mL) and water (1.7 mL). The mixture was reacted according to General Procedure E. The crude residue was purified using Biotage silica gel chromatography (0-35% ethyl acetate in hexanes) to afford the title compound (0.26 g, 0.79 mmol, 36% yield). MS (ESI) m/z 331.4 [M+1]+.

Workup

  1. customIn a microwave flask was placed
  2. customThe mixture was reacted
  3. customThe crude residue was purified

Sources & evidence

ORD record
ord-6a535461221245d394f339696c59573b
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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