Toluene → HCID 69318448, compound

HRID 1793245Notes

Reaction equation

HRID 1793245 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11](Cl)[N:10]=2)[CH:5]=[CH:4][N:3]=1.[CH:16]([Sn](CCCC)(CCCC)CCCC)=[CH2:17].[C:31]1(C)C=CC=C[CH:32]=1>CCOC(C)=O.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>[CH:16]([C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH:31]=[CH2:32])[N:10]=2)[CH:5]=[CH:4][N:3]=1)=[CH2:17]

Participants

6

Reactant 3

HCID 1140TolueneHCID 81998TributylvinyltinHCID 22326907HCID 22326907, compound

Product 1

HCID 69318448HCID 69318448, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

The 2-chloropyrimidinyl ether intermediate (500 mg, 0.896 mmol) (see Example 1), vinyltributyltin (600 mg, 1.89 mmol), BHT (20 mg), and (PPh3)4Pd (50 mg, 0.045 mmol) were suspended in degassed toluene (10 mL) under argon and heated to 115° C. for 3 h. The reaction mixture was cooled, diluted with EtOAc (100 mL), washed with brine (10 mL), and dried over MgSO4. Silica gel chromatography (gradient elution, 0% to 80% EtOAc in hexanes) provided the desired 2-vinylpyrimidinyl ether intermediate (302 mg, 61%) as a pale yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with brine (10 mL)
  3. dry with materialdried over MgSO4
  4. washSilica gel chromatography (gradient elution, 0% to 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4a68867ef8f04e06881a1c8b1485ab02
Source dataset
uspto-grants-2006_07
Patent number
US07078419B2

Reaction notes

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