Sodium Carbonate → N-Methyl-5-[6-morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-2-yl]pyrimidin-2-amine

HRID 421323ノート

反応式

HRID 421323 の反応式
O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:13][NH:14][C:15]1[N:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][N:16]=1.Cl[C:31]1[N:39]=[C:38]2[C:34]([N:35]=[CH:36][N:37]2[CH2:40][CH:41]2[CH2:45][CH2:44][O:43][CH2:42]2)=[C:33]([N:46]2[CH2:51][CH2:50][O:49][CH2:48][CH2:47]2)[N:32]=1>O>[CH3:13][NH:14][C:15]1[N:16]=[CH:17][C:18]([C:31]2[N:39]=[C:38]3[C:34]([N:35]=[CH:36][N:37]3[CH2:40][CH:41]3[CH2:45][CH2:44][O:43][CH2:42]3)=[C:33]([N:46]3[CH2:47][CH2:48][O:49][CH2:50][CH2:51]3)[N:32]=2)=[CH:19][N:20]=1

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 467396412-Methylaminopyrimidine-5-boronic acid, pinacol esterHCID 593335062-Chloro-6-morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purine

生成物 1

HCID 59333550N-Methyl-5-[6-morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-2-yl]pyrimidin-2-amine収率 41%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

1,4-Dioxane (40 ml), water (20 ml), and sodium carbonate (2 g, 19 mmol) were added to N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (1.45 g, 6.18 mmol) and 2-chloro-6-morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purine (2.0 g, 6.18 mmol) and the atmosphere in the reaction vessel was substituted with nitrogen. Tetrakis triphenylphosphine palladium (0.36 g, 0.31 mmol) was added, then the atmosphere in the reaction vessel was substituted with nitrogen again, and the resulting mixture was heated to reflux for 3 hours. The reaction mixture was partitioned with ethyl acetate and water, the organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. Methylene chloride-ether was added to the residue and the insoluble matter was collected by filtration and dried to give the title compound (1.0 g, 41%) as a white solid.

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe reaction mixture was partitioned with ethyl acetate and water
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionMethylene chloride-ether was added to the residue
  7. filtrationthe insoluble matter was collected by filtration
  8. customdried

出典と根拠

ORDレコード
ord-d8a1a4dcc3434ae682434e45b9b22bc4
出典データセット
uspto-grants-2012_01
特許番号
US08097622B2

反応ノート

読み込み中…