ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

4,6-Dichloro-2-methylpyrimidine → 2-{6-[(6-Chloro-2-methylpyrimidin-4-yl)oxy]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,6-dimethyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

HRID 885990
ノート
印刷プレビュー

反応式

HRID 885990 の反応式
[CH3:1][C:2]1([CH3:23])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1.[Cl:24][C:25]1[CH:30]=[C:29](Cl)[N:28]=[C:27]([CH3:32])[N:26]=1.CC(C)([O-])C.[Na+]>C1COCC1>[Cl:24][C:25]1[N:26]=[C:27]([CH3:32])[N:28]=[C:29]([O:22][C:19]2[CH:20]=[CH:21][C:16]3[O:15][CH2:14][CH2:13][N:12]([C:10]4[S:9][C:5]5[C:6](=[O:8])[NH:7][C:2]([CH3:23])([CH3:1])[CH2:3][C:4]=5[N:11]=4)[C:17]=3[CH:18]=2)[CH:30]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 2349974,6-Dichloro-2-methylpyrimidineHCID 23676156Sodium t-butoxideHCID 671855836,6-Dimethyl-2-(6-hydroxy-2,3-dihydrobenzo[1,4]oxazin-4-yl)-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

生成物 1

HCID 248558182-{6-[(6-Chloro-2-methylpyrimidin-4-yl)oxy]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,6-dimethyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one収率 35%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
155 °C

実験手順

To a suspension of Example 57 (70 mg, 0.211 mmol) in THF (4 mL) was added 4,6-dichloro-2-methylpyrimidine (86 mg, 0.529 mmol) and sodium tert-butoxide (81 mg, 0.846 mmol). The reaction was heated to 155° C. under microwave irradiation for 30 minutes then cooled to room temperature. The mixture was partitioned between DCM (50 mL) and water (50 mL); the organic phase was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo. The residue was purified by preparative HPLC (Method 6) to give the title compound (32 mg, 35%) as an off-white solid. δH (CDCl3) 8.02 (1H, d, J 2.8 Hz), 6.99 (1H, d, J 8.9 Hz), 6.82 (1H, dd, J 8.9 and 2.6 Hz), 6.66 (1H, s), 5.50 (1H, s), 4.47-4.26 (2H, m), 4.19-4.04 (2H, m), 2.86 (2H, s), 2.61 (3H, s), 1.38 (6H, s). LCMS (ES+) 458.0 (M+H)+, RT 3.50 minutes (Method 1).

後処理

  1. temperaturethen cooled to room temperature
  2. customThe mixture was partitioned between DCM (50 mL) and water (50 mL)
  3. washthe organic phase was washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative HPLC (Method 6)

出典と根拠

ORDレコード
ord-66f80fb4eb0e459287bdd6688f5853b9
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08242116B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート