Dimethylformamide → 4-Chloro-6-(5-chloro-2-methoxyphenyl)-2-methylpyrimidine

HRID 28556

반응식

HRID 28556 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([C:8]2[N:13]=[C:12]([CH3:14])[NH:11][C:10](=O)[CH:9]=2)[CH:7]=1.CN(C)C=O.C(Cl)(=O)C([Cl:26])=O>ClCCl.O1CCOCC1>[Cl:26][C:10]1[CH:9]=[C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:16][CH3:17])[N:13]=[C:12]([CH3:14])[N:11]=1

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1363418886-(5-Chloro-2-methoxyphenyl)-2-methylpyrimidin-4-ol

생성물 1

HCID 656453264-Chloro-6-(5-chloro-2-methoxyphenyl)-2-methylpyrimidine수율 94%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 312751,4-Dioxane용매

실험 절차

To a suspension of 6-(5-chloro-2-methoxy-phenyl)-2-methyl-3H-pyrimidin-4-one (520 mg, 2.1 mmol) in dichloromethane (20 ml) and 1,4-dioxane (20 ml) was added N,N-dimethylformamide (0.2 ml) followed by a solution of oxalyl chloride in dichloromethane (2 M, 4.2 ml). After stirring for 1 hour, the mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate solution (60 ml). The organic phase was dried over magnesium sulfate and concentrated under vacuum to give 4-chloro-6-(5-chloro-2-methoxy-phenyl)-2-methyl-pyrimidine (530 mg, 94% yield) as a white powder. 1H NMR (DMSO-d6) δ 2.67 (s, 3H, CH3), 3.91 (s, 3H, CH3), 7.26 (d, 1H, J=9.2 Hz, Ar), 7.59 (dd, 1H, J=8.8 Hz, J=2.6 Hz, Ar), 7.95 (s, 1H, Ar), 7.96 (d, 1H, J=2.9 Hz, Ar).

후처리

  1. concentrationthe mixture was concentrated under vacuum
  2. customThe residue was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate solution (60 ml)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-4749b9b34d4d42a3a1c43ccca0c7b463
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419984B2

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