Sodium Carbonate → HCID 53328599, compound

HRID 628977Notes

Reaction equation

HRID 628977 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([O:12][CH2:13][CH3:14])=[C:10]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:9]=[C:8](Cl)[N:7]=1)=[O:5])[CH3:2].CC1(C)C(C)(C)OB([C:30]2[CH:31]=[C:32]([OH:36])[CH:33]=[CH:34][CH:35]=2)O1.O1CCOCC1.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>[CH2:1]([O:3][C:4]([C:6]1[C:11]([O:12][CH2:13][CH3:14])=[C:10]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:9]=[C:8]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27346233-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 86723553HCID 86723553, compound

Product 1

HCID 53328599HCID 53328599, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-chloro-5-ethoxy-6-morpholine-4-yl-pyrimidine-4-carboxylic acid ethyl ester (152 mg, 1 eq.), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (137.9 mg, 1.3 eq.), dioxane (6 ml), H2O (1 ml), Pd(PPh3)4 (56 mg, 0.1 eq.) and sodium carbonate (102 mg, 2 eq.) was heated to reflux overnight. The solvent was removed in vacuo. The residue was extracted with EA, and the organic layer washed with brine and dried. The crude was purified by chromatography to give a product (99.6 mg, 55%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed in vacuo
  4. extractionThe residue was extracted with EA
  5. washthe organic layer washed with brine
  6. customdried
  7. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-29729c5c87074a47af687a6ba73cc4a8
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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