4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile → trans-4-(3-Hydroxy-cyclopentylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrile

HRID 2386681ノート

反応式

HRID 2386681 の反応式
[NH2:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([OH:7])[CH2:3]1.Cl[C:9]1[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=1>C1COCC1>[OH:7][C@H:4]1[CH2:5][CH2:6][C@H:2]([NH:1][C:9]2[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=2)[CH2:3]1

参加物

4

反応物 2

HCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 42614395(1S,3S)-3-Aminocyclopentan-1-ol

生成物 1

HCID 66955848trans-4-(3-Hydroxy-cyclopentylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrile収率 66.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

TEA (0.84 mL, 6.04 mmol) was added to a solution of trans-3-amino-cyclopentanol (1.83 g) in anhydrous THF (10 mL), under argon atmosphere. 4-Chloro-2-methylsulfanyl-pyrimidine-5-carbonitrile (1.13 g, 6.04 mmol) was then added in two portions and the resulting mixture was stirred, at RT, under argon atmosphere, for 2 h. The liquid layer was decanted and THF was added to the gummy residue. The extraction procedure was repeated and the combined extracts were evaporated under reduced pressure. The crude residue was absorbed onto silica gel and purified by flash chromatography (EtOAc/hexane) to give 1.0 g of trans-4-(3-hydroxy-cyclopentylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrile.

後処理

  1. customThe liquid layer was decanted
  2. additionTHF was added to the gummy residue
  3. extractionThe extraction procedure
  4. customthe combined extracts were evaporated under reduced pressure
  5. customThe crude residue was absorbed onto silica gel
  6. custompurified by flash chromatography (EtOAc/hexane)

出典と根拠

ORDレコード
ord-820c612e17a34546967f0072a2485de8
出典データセット
uspto-grants-2012_09
特許番号
US08268840B2

反応ノート

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