N-bromobutanimide → 3-[5-bromo-4-[(2,4-difluorobenzyl)oxy]-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoic acid

HRID 1713225ノート

反応式

HRID 1713225 の反応式
[F:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[CH2:4][O:5][C:6]1[N:7]=[CH:8][N:9]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:16]([OH:18])=[O:17])[C:10](=[O:12])[CH:11]=1.C1C(=O)N([Br:35])C(=O)C1>C(Cl)Cl>[Br:35][C:11]1[C:10](=[O:12])[N:9]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:16]([OH:18])=[O:17])[CH:8]=[N:7][C:6]=1[O:5][CH2:4][C:3]1[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:2]=1[F:1]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 210889853-[4-[(2,4-difluorobenzyl)oxy]-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoic acid

生成物 1

HCID 210892753-[5-bromo-4-[(2,4-difluorobenzyl)oxy]-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a cooled (0° C.) solution of 3-[4-[(2,4-difluorobenzyl)oxy]-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoic acid (5.76 g, 15.5 mmol) in DCM (35 mL) was added NBS (2.48 g, 13.9 mmol). Allowed reaction to warm to ambient temperature. After 5 h, cooled (0° C.) reaction mixture, filtered solid, washed with cold DCM and cold hexane, and dried in vacuo. Obtained product as orange solid (5.57 g, 80%). Used without further purification. 1H NMR (CD3OD/400 MHz) δ8.29 (s, 1H), 8.05 (m, 1H), 7.91 (s, 1H), 7.60 (q, 1H, J=8.0 Hz), 7.51 (d, 1H, J=8.0 Hz), 6.99 (m, 2H), 5.57 (s, 2H), 2.17 (s, 3H). ESHRMS m/z 451.0095 (M+H calculated for C19H14BrF2N2O4 requires 451.0100).

後処理

  1. customAllowed reaction
  2. temperaturecooled
  3. custom(0° C.) reaction mixture
  4. filtrationfiltered solid
  5. washwashed with cold DCM and cold hexane
  6. customdried in vacuo
  7. customUsed without further purification

出典と根拠

ORDレコード
ord-4bcb20c8d39145afbc11045a0bf19b96
出典データセット
uspto-grants-2010_09
特許番号
US07795271B2

反応ノート

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