Ethyl Acrylate → Ethyl (E)-3-(2-chloropyrimidin-5-yl)acrylate

HRID 226392Notes

Reaction equation

HRID 226392 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:31]([O:35][CH2:36][CH3:37])(=[O:34])[CH:32]=[CH2:33].C(N(CC)C(C)C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5](/[CH:33]=[CH:32]/[C:31]([O:35][CH2:36][CH3:37])=[O:34])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 17142232-Chloro-5-iodopyrimidine

Product 1

HCID 53259409Ethyl (E)-3-(2-chloropyrimidin-5-yl)acrylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-chloro-5-iodopyrimidine (7.62 g), palladium(II) acetate (356 mg), tri(o-tolyl)phosphine (965 mg), and DMF (32 mL) was added ethyl acrylate (17.2 mL) and N,N-diisopropylethylamine (13.8 mL). After stirring for 3 hours at 100° C., the reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E)-3-(2-chloro-5-pyrimidinyl)acrylate (2.32 g).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and H2O
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b212646e797944888b766c08bba54603
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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