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

HRID 2386681Notes

Reaction equation

HRID 2386681 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-820c612e17a34546967f0072a2485de8
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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