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2-Mesitylenesulfonyl chloride → 2-Amino-5-(4-(hydroxymethyl)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

HRID 2207062
ノート
印刷プレビュー

反応式

HRID 2207062 の反応式
[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9](Cl)(=[O:11])=[O:10].C(N(C(C)C)CC)(C)C.[NH2:23][C:24]1[N:29]=[C:28]([OH:30])[C:27]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38][OH:39])=[CH:34][C:33]=2[O:40][CH3:41])=[C:26]([CH3:42])[N:25]=1>C1COCC1.O>[CH3:13][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:30][C:28]1[C:27]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38][OH:39])=[CH:34][C:33]=2[O:40][CH3:41])=[C:26]([CH3:42])[N:25]=[C:24]([NH2:23])[N:29]=1)(=[O:11])=[O:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 130462-Mesitylenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178492557HCID 178492557、化合物

生成物 1

HCID 879451512-Amino-5-(4-(hydroxymethyl)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate収率 84.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

2-Mesitylenesulfonyl chloride (7.2 g) was added to a suspension of diisopropylethylamine (5.5 mL) and the product from step (iii) (6.1 g) in THF (200 mL) and the mixture was stirred under reflux for 12 h. The resulting mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed with brine, dried and concentrated under reduced pressure. The residue was purified by flash column chromatography on amino silica gel to afford the sub-title compound (8.6 g) as a white solid; 1H NMR (300 MHz, CDCl3); 6.92 (2H, s), 6.86 (1H, s), 6.77 (2H, s), 4.67 (2H, br s), 4.64 (2H, d), 3.82 (3H, s), 3.81 (2H, s), 2.57 (6H, s), 2.29 (3H, s), 2.21 (3H, s), 1.81 (1H, t).

後処理

  1. temperatureunder reflux for 12 h
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography on amino silica gel

出典と根拠

ORDレコード
ord-df674a0063ca4e19ad7a93671e2187e2
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09376398B2

反応ノート

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