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

HRID 2228918ノート

反応式

HRID 2228918 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒

反応条件

温度
135 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-189b6f8cbb934fb28df7a4189ba84186
出典データセット
uspto-grants-2002_07
特許番号
US06417192B1

反応ノート

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