Potassium Phosphate, Tribasic → HCID 178488539, compound

HRID 2169221Notes

Reaction equation

HRID 2169221 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=2Br)[N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O)CCC.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:1]([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 178488296tert-butyl 2-[(2-bromo-5-methoxyphenyl)methyl]-4-oxo-5-phenylmethoxy-1H-pyrimidine-6-carboxylate

Product 1

HCID 178488539HCID 178488539, compoundYield 56.94%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 22253497Water butanolSolvent

Procedure

To a stirred solution of 5-benzyloxy-2-(2-bromo-5-methoxybenzyl)-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (138) (3 g, 5.988 mmol) in n-butanol:water (3:1, 12 mL) were added phenyl boronic acid (1.096 g, 8.982 mmol), X-Phos (427 mg, 0.898 mmol), K3PO4 (4.44 g, 20.958 mmol) and Pd(dba)2 (275 mg, 0.479 mmol). The reaction mixture was refluxed for 10 h. After completion of the reaction, the mixture was evaporated to get a crude product which was purified by a normal silica column using 2% methanol in dichloromethane to afford 5-benzyloxy-6-hydroxy-2-(4-methoxybiphenyl-2-ylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (139) (1.7 g, 56.94%) as an off-white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 10 h
  2. customAfter completion of the reaction
  3. customthe mixture was evaporated
  4. customto get a crude product which
  5. customwas purified by a normal silica column

Sources & evidence

ORD record
ord-84d8c9c281ee4dbeaf5be15e439850ea
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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