Potassium Phosphate, Tribasic → 3-benzyl-5-(3-fluoro-4-methoxyphenyl)-2-(methylthio)pyrimidin-4(3H)-one

HRID 2246474Notes

Reaction equation

HRID 2246474 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12](Br)=[CH:11][N:10]=[C:9]1[S:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:21]2[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:19]([F:18])[CH:20]=2)=[CH:11][N:10]=[C:9]1[S:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 592183763-benzyl-5-bromo-2-(methylthio)pyrimidin-4(3H)-one

Product 1

HCID 592183693-benzyl-5-(3-fluoro-4-methoxyphenyl)-2-(methylthio)pyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

In a separate flask, 3-benzyl-5-bromo-2-(methylthio)pyrimidin-4(3H)-one (580.5 mg, 1.87 mmol), tris(dibenzylideneacetone)dipalladium (0) (65.0 mg, 0.0710 mmol), 3-fluoro-4-methoxyphenylboronic acid (492.3 mg, 2.90 mmol), S-Phos (97.7 mg, 0.238 mmol), and potassium phosphate (1.250 g, 5.89 mmol) were suspended in toluene (15 ml) and nitrogen was bubbled through for about 30 seconds. The flask was fitted with a reflux condenser and placed in a preheated oil bath (100 C) and stirred under nitrogen for 105 minutes. The reaction was then cooled to room temperature and allowed to stand overnight.

Workup

  1. customnitrogen was bubbled through for about 30 seconds
  2. customThe flask was fitted with a reflux condenser
  3. customplaced in a preheated oil bath
  4. waitto stand overnight

Sources & evidence

ORD record
ord-be0ddb2724da4cc8b9a00d7a370b1256
Source dataset
uspto-grants-2010_03
Patent number
US07687522B2

Reaction notes

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