Potassium Carbonate → 5-(Benzyloxy)-4-chloro-6-p-tolylpyrimidine

HRID 1912646Notes

Reaction equation

HRID 1912646 reaction equation
[CH2:1]([O:8][C:9]1[C:10](Cl)=[N:11][CH:12]=[N:13][C:14]=1[Cl:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].B(O)(O)[C:24]1[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=1>C1(C)C=CC=CC=1.O.COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[C:14]([Cl:15])=[N:13][CH:12]=[N:11][C:10]=1[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 583080995-(Benzyloxy)-4,6-dichloropyrimidine

Product 1

HCID 866659375-(Benzyloxy)-4-chloro-6-p-tolylpyrimidineYield 35.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 131731093PhMe H2O DMESolvent

Conditions

Temperature
100 °C

Procedure

The compound from step 3 (12.78 g, 0.05 mol) was dissolved in (4:1:1) PhMe/H2O/DME (111 ml). Pd(Ph3P)4 (2.9 g, 0.05 eq), K2CO3, and p-tolylboronic acid (6.81 g, 1 eq) were added, the mixture was degassed and heated at 100° C. overnight. After cooling to room temperature the organic layer was purified by silica gel chromatography (0-10% EtOAc in hexane) to give 5.5 g of the title compound.

Workup

  1. customthe mixture was degassed
  2. temperatureAfter cooling to room temperature the organic layer
  3. customwas purified by silica gel chromatography (0-10% EtOAc in hexane)

Sources & evidence

ORD record
ord-a992c9aa7d46467f98590f61c2764cf9
Source dataset
uspto-grants-2013_12
Patent number
US08609676B2

Reaction notes

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