Sodium Carbonate → 2-(2-chloro-4-pyrimidinyl)-6-methylPhenol

HRID 530420Notes

Reaction equation

HRID 530420 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.O1CCOCC1.[OH:15][C:16]1[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>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.O>[Cl:1][C:2]1[N:7]=[C:6]([C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([CH3:22])[C:16]=2[OH:15])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 775312,4-DichloropyrimidineHCID 18616946(2-Hydroxy-3-methylphenyl)boronic acid

Product 1

HCID 1371315312-(2-chloro-4-pyrimidinyl)-6-methylPhenol

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3.0 g (20 mmol) of 2,4-dichloro-pyrimidine in a 10:1 mixture of dioxane:water (220 mL) is added 3.3 g (22 mmol) of 2-hydroxy-3-methyl-phenyl boronic acid followed by 6.0 g (57 mmol) of sodium carbonate. Argon is bubbled through the solution for 15 min then 2.4 g (2.1 mmol) of tetrakis(triphenylphosphine)palladium (0) is added. The reaction is heated overnight at 100° C. then cooled to ambient temperature and filtered through diatomaceous earth. The filter pad is washed with EtOAc then placed on a new receiving flask and washed with a 1:1 mixture of MeOH:DCM. The filtrate is concentrated under reduced pressure to B-16 (1.60 g, 36.0%)

Workup

  1. customArgon is bubbled through the solution for 15 min
  2. temperaturethen cooled to ambient temperature
  3. filtrationfiltered through diatomaceous earth
  4. washThe filter pad is washed with EtOAc
  5. washwashed with a 1:1 mixture of MeOH
  6. concentrationThe filtrate is concentrated under reduced pressure to B-16 (1.60 g, 36.0%)

Sources & evidence

ORD record
ord-e719394409a34fa2bfe7bb57a1b3fcb8
Source dataset
uspto-grants-2016_05
Patent number
US09353090B2

Reaction notes

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