Sodium Carbonate → 5-[9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]-N-methylpyrimidin-2-amine

HRID 1876508ノート

反応式

HRID 1876508 の反応式
C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.Cl[C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH2:23][CH:24]2[CH2:26][CH2:25]2)=[C:16]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:15]=1.[CH3:33][NH:34][C:35]1[N:40]=[CH:39][C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][N:36]=1>C(OCC)(=O)C.O>[CH:24]1([CH2:23][N:20]2[CH:19]=[N:18][C:17]3[C:21]2=[N:22][C:14]([C:38]2[CH:37]=[N:36][C:35]([NH:34][CH3:33])=[N:40][CH:39]=2)=[N:15][C:16]=3[N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH2:26][CH2:25]1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 467396412-Methylaminopyrimidine-5-boronic acid, pinacol esterHCID 593335522-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purine

生成物 1

HCID 593336695-[9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]-N-methylpyrimidin-2-amine収率 61%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Sodium carbonate (2.40 g, 22.7 mmol) and tetrakis triphenylphosphine palladium (0.44 g, 0.38 mmol) were added to a 1,4-dioxane (44.0 ml)-water (22.0 ml) mixture solution of 2-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purine (2.22 g, 7.56 mmol) and 2-methylaminopyrimidine-5-boronic acid pinacol ester (2.31 g, 9.82 mmol) at room temperature and the resulting mixture was heated to reflux for 3.5 hours in an argon atmosphere. The reaction mixture was left standing to cool and then poured into water and ethyl acetate was added to separate the layers. The solid precipitated in the aqueous layer was collected by filtration, washed with water, and then dried at 50° C. under reduced pressure. Meanwhile, the organic layer was dried over anhydrous sodium sulfate, the mixture was filtrated, then the filtrate was concentrated under reduced pressure, and the resulting solid was washed with dichloromethane and collected by filtration. These solids were combined to give the title compound (1.68 g, 61%) as a white solid.

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 3.5 hours in an argon atmosphere
  3. waitThe reaction mixture was left
  4. temperatureto cool
  5. additionwas added
  6. customto separate the layers
  7. customThe solid precipitated in the aqueous layer
  8. filtrationwas collected by filtration
  9. washwashed with water
  10. customdried at 50° C. under reduced pressure
  11. dry with materialMeanwhile, the organic layer was dried over anhydrous sodium sulfate
  12. filtrationthe mixture was filtrated
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. washthe resulting solid was washed with dichloromethane
  15. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-067a5c28dc634432b80dd7711539ca5d
出典データセット
uspto-grants-2012_11
特許番号
US08309546B2

反応ノート

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