Sodium Bicarbonate → (3S)-3-(aminomethyl)-3-cyclopropyl-1-(2-((1-(1-hydroxy-2-methylpropan-2-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)pyrrolidin-2-one

HRID 714908ノート

反応式

HRID 714908 の反応式
[CH:1]1([C@:4]2([C:27]#[N:28])[CH2:8][CH2:7][N:6]([C:9]3[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]4[CH:17]=[N:18][N:19]([C:21]([CH3:25])([CH3:24])[CH2:22][OH:23])[CH:20]=4)[N:10]=3)[C:5]2=[O:26])[CH2:3][CH2:2]1.[BH4-].[Na+].C(=O)([O-])O.[Na+]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[NH2:28][CH2:27][C@@:4]1([CH:1]2[CH2:3][CH2:2]2)[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:17]=[N:18][N:19]([C:21]([CH3:25])([CH3:24])[CH2:22][OH:23])[CH:20]=3)[N:10]=2)[C:5]1=[O:26]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 71741336(3S)-3-cyclopropyl-1-(2-((1-(1-hydroxy-2-methylpropan-2-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-2-oxopyrrolidine-3-carbonitrile

生成物 1

HCID 117841033(3S)-3-(aminomethyl)-3-cyclopropyl-1-(2-((1-(1-hydroxy-2-methylpropan-2-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)pyrrolidin-2-one収率 20.8%

試薬・触媒・溶媒 2

HCID 517166Dichlorocobalt hexahydrate触媒HCID 887Methanol溶媒

実験手順

To a solution of (3S)-3-cyclopropyl-1-(2-((1-(1-hydroxy-2-methylpropan-2-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-2-oxopyrrolidine-3-carbonitrile (400 mg) obtained in Step I of Example 103 and cobalt(II) chloride hexahydrate (1.0 g) in methanol (6.0 mL) was added sodium borohydride (400 mg), and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution in an ice bath, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (84 mg).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

出典と根拠

ORDレコード
ord-8d8f62c591d645f1bc7cfe50c20cf7a4
出典データセット
uspto-grants-2015_11
特許番号
US09187453B2

反応ノート

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