Ethyl Acetate → 5-Bromo-2-chloro-4-(2-ethoxyphenoxy)pyrimidine

HRID 1042745

반응식

HRID 1042745 반응식
[H-].[Na+].[O:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])[CH2:4][CH3:5].[Br:13][C:14]1[C:15](Cl)=[N:16][C:17]([Cl:20])=[N:18][CH:19]=1.CCOC(C)=O>CN(C=O)C.CC#N>[Br:13][C:14]1[C:15]([O:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:3][CH2:4][CH3:5])=[N:16][C:17]([Cl:20])=[N:18][CH:19]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 667552-EthoxyphenolHCID 2899735-Bromo-2,4-dichloropyrimidine

생성물 1

HCID 790765415-Bromo-2-chloro-4-(2-ethoxyphenoxy)pyrimidine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매2회

실험 절차

To a suspension of NaH (0.42 g 60% in mineral oil, 10.5 mmol) in DMF (8.0 mL) was slowly added 2-ethoxylphenol (1.34 g, 9.7 mmol) in MeCN (4.0 mL) at 0° C. under N2. After the addition, the reaction mixture was allowed to warm up to room temperature for 0.5 hour. 5-bromo-2,4-dichloropyrimidine (2.0 g, 8.8 mmol) in MeCN (16.0 mL) was slowly added and then the resulting reaction mixture was stirred at room temperature for 24 hour. EtOAc (120 mL) was added and washed with NaOH (30 mL, 0.5N) and brine (25×2 mL). The organic layer was dried with MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10% to 30% EtOAc in Hexanes, gradient elution) to provide the 5-bromo-2-chloro-4-(2-ethoxyphenoxy)pyrimidine. MS m/z=330 [M+1]+. Calc'd for: C12H10BrClN2O2: 329

후처리

  1. customat 0° C.
  2. additionAfter the addition
  3. customthe resulting reaction mixture
  4. washwashed with NaOH (30 mL, 0.5N) and brine (25×2 mL)
  5. dry with materialThe organic layer was dried with MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (10% to 30% EtOAc in Hexanes, gradient elution)

출처 및 근거

ORD 기록
ord-ea489643db744541870091d3137221ac
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557996B2

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