Sodium Iodide → 2-Amino-4-chloro-6-pyrimidylacetonitrile

HRID 230984ノート

反応式

HRID 230984 の反応式
C(OC(=O)C[C:8]1[C:9]([Cl:17])=[N:10][C:11]([NH2:16])=[N:12][C:13]=1[C:14]#N)(C)(C)C.[I-].[Na+].Cl[Si](C)(C)C.[C:26](#[N:28])C>>[NH2:16][C:11]1[N:10]=[C:9]([Cl:17])[CH:8]=[C:13]([CH2:14][C:26]#[N:28])[N:12]=1

参加物

5

反応物 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 539121792-Amino-4-chloro-6-cyano-pyrimidylacetate-t-butyl ester

生成物 1

HCID 159259282-Amino-4-chloro-6-pyrimidylacetonitrile

反応条件

温度
40 °C

実験手順

2-amino-4-chloro-6-cyano-pyrimidylacetate-t-butyl ester (100 g, 372.5 mmol) was suspended in dry acetonitrile (1.2 l) containing sodium iodide (55.84 g, 372.5 mmol) and warmed to 40° C. until the mixture became homogeneous. Then chlorotrimethylsilane (200 ml) was added and the orange suspension was heated at reflux. After 1 hour, TLC analysis (elute with 1:1 ethyl acetate/hexanes) indicated a complete reaction and the reaction was filtered and the filtrate was concentrated. The residue was diluted with ethyl acetate and washed with water and sodium bicarbonate solution and dried with magnesium sulfate. The crude product was slurried in activated carbon, filtered and concentrated to give 38.46 g of a green solid. This was again dissolved in ethyl acetate and passed through a 4-inch pad of silica gel and then concentrated to give the desired subject as a green solid, m.p. 110°-115° C. NMR (200 mHz) D6-acetone δ 6.8 (s, 1 H), 6.8-6.6 (bs, 1 H), 3.95 (s, 2 H).

後処理

  1. temperaturethe orange suspension was heated
  2. temperatureat reflux
  3. washTLC analysis (elute with 1:1 ethyl acetate/hexanes)
  4. customa complete reaction
  5. filtrationthe reaction was filtered
  6. concentrationthe filtrate was concentrated
  7. additionThe residue was diluted with ethyl acetate
  8. washwashed with water and sodium bicarbonate solution
  9. dry with materialdried with magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-84325f7a73134de28703c120f054c11c
出典データセット
uspto-grants-1989_07
特許番号
US04844727

反応ノート

読み込み中…