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Sodium hydride → 5-[Cyano-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methyl]-isophthalonitrile

HRID 426278
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HRID 426278 반응식
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([C:12]#[N:13])[CH:7]=[C:8]([CH:11]=1)[C:9]#[N:10])#[N:2].Cl[C:15]1[C:20]([CH:21]([CH3:23])[CH3:22])=[C:19]([O:24][CH3:25])[N:18]=[C:17]([O:26][CH3:27])[N:16]=1.[H-].[Na+]>CN(C=O)C>[C:1]([CH:3]([C:15]1[C:20]([CH:21]([CH3:23])[CH3:22])=[C:19]([O:24][CH3:25])[N:18]=[C:17]([O:26][CH3:27])[N:16]=1)[C:4]1[CH:11]=[C:8]([C:9]#[N:10])[CH:7]=[C:6]([CH:5]=1)[C:12]#[N:13])#[N:2]
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 160881865-Isopropyl-6-chloro-2,4-dimethoxypyrimidineHCID 667055675-Cyanomethyl-isophthalonitrile

생성물 1

HCID 591847545-[Cyano-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methyl]-isophthalonitrile수율 43%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

5-Cyanomethyl-isophthalonitrile (0.285 g, 1.70 mmol) and 4-chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (0.360 g, 1.66 mmol) was dissolved in DMF (8.0 mL) and cooled to 0° C. 60% Sodium hydride (0.136 g, 3.40 mmol) was added portionwise and the reaction was stirred at 0° C. for 2 h, then rt overnight. The reaction was quenched with saturated ammonium chloride solution and pH was adjusted to ˜6.0 with 1N HCl. Mixture was extracted with ethyl acetate and organic layer was dried (MgSO4) and concentrated. The resulting residue was purified by flash column chromatography (silica gel, 10 to 50% ethyl acetate/hexane) to give a white solid (0.2457 g, 43%). 1H NMR (300 MHz, CDCl3): δ 7.90 (s, 3H), 5.46 (s, 1H), 3.96 (s, 3H), 3.89 (s, 3H), 3.05-2.9 (m, 1H), 1.16 (d, J=6.9 Hz, 3H), 1.15 (d, J=7.2 Hz, 3H).

후처리

  1. customrt overnight
  2. customThe reaction was quenched with saturated ammonium chloride solution and pH
  3. extractionMixture was extracted with ethyl acetate and organic layer
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash column chromatography (silica gel, 10 to 50% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-6fc24924f44c46e9b752ce10f90c2dc6
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08106064B2

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