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

HRID 2386681노트

반응식

HRID 2386681 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-820c612e17a34546967f0072a2485de8
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268840B2

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