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

HRID 230984노트

반응식

HRID 230984 반응식
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

참가 물질

5

반응물 4

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

생성물 1

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

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-84325f7a73134de28703c120f054c11c
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04844727

반응 노트

불러오는 중…