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

HRID 28556

反応式

HRID 28556 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4749b9b34d4d42a3a1c43ccca0c7b463
出典データセット
uspto-grants-2008_09
特許番号
US07419984B2

関連ノート

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