Triethylamine → Ethyl 3-(2-methoxypyrimidin-5-yl)acrylate

HRID 2228918Notes

Reaction equation

HRID 2228918 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6](Br)=[CH:5][N:4]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:12]=[CH:11][C:10]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 139657Pyrimidine, 5-bromo-2-methoxy-

Product 1

HCID 53940995Ethyl 3-(2-methoxypyrimidin-5-yl)acrylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2-methoxy-5-bromopyrimidine (75.43 g, 0.399 mol), ethyl acrylate (47.5 ml, 0.439 mol), palladium (II) acetate (1.07 g, 0.0048 mol), tri-o-tolylphosphine (2.92 g, 0.0096 mol) and triethylamine (84 ml) were heated at 135° C. with stirring under argon for 12 h. After allowing to cool the solid mass was dissolved in water and ethyl acetate, filtered, and the aqueous phase separated and further extracted with ethyl acetate. The combined extracts were washed with saturated aqueous ammonium chloride, dried (MgSO4) and evaporated. The solid thus obtained was triturated with ether/light petrol (1:3, 350 ml), filtered, washed and dried, yield 52.41 g (63%). 1H-NMR (CDCl3) δ 1.33 (3H, t), 4.06 (3H, s), 4.28 (2H, q), 6.45 (1H, d), 7.58 (1H, d), 8.67 (2H, s); MS (APCI+) found (M+H)=209; C10H12N2O3 requires 208.

Workup

  1. temperatureto cool the solid mass
  2. filtrationethyl acetate, filtered
  3. customthe aqueous phase separated
  4. extractionfurther extracted with ethyl acetate
  5. washThe combined extracts were washed with saturated aqueous ammonium chloride
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe solid thus obtained
  9. customwas triturated with ether/light petrol (1:3, 350 ml)
  10. filtrationfiltered
  11. washwashed
  12. customdried

Sources & evidence

ORD record
ord-189b6f8cbb934fb28df7a4189ba84186
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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