Potassium Phosphate, Tribasic → HCID 57474620, compound

HRID 391636Notes

Reaction equation

HRID 391636 reaction equation
[NH2:1][C:2]1[C:3]([C:19]([O-:21])=O)=[N:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)=[N:6][C:7]=1[NH:8][CH:9]([CH3:11])[CH3:10].[NH2:22]C1C(C([O-])=O)=NC(Cl)=NC=1NC(C)C.[OH:37][C:38]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>[CH:9]([N:8]1[C:38](=[O:37])[NH:1][C:2]2[C:7]1=[N:6][C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1)=[N:4][C:3]=2[C:19]([NH2:22])=[O:21])([CH3:10])[CH3:11]

Participants

9

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57474623HCID 57474623, compoundHCID 178456837HCID 178456837, compound

Product 1

HCID 57474620HCID 57474620, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-6-isopropylamino-2-(3-hydroxy-phenyl)-pyrimidine-4-carboxylate. In a microwave flask was placed 5-amino-6-isopropylamino-2-chloro-pyrimidine-4-carboxylate (1.2 g, 4.6 mmol), 3-hydroxyphenylboronic acid (0.96 g, 7.0 mmol), potassium phosphate (3.0 g, 14.0 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.28 g, 0.68 mmol) and palladium (II) acetate (0.16 g, 0.71 mmol) in tetrahydrofuran (25 mL) and water (4 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 (0.43 g, 1.4 mmol, 29% yield). MS (ESI) m/z 317.1 [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-62bdd543ad06490c8762b75a06d2f6d5
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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