Methanol → ((3S)-1-((3-methyl-4-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methylsulfonyl)pyrrolidin-3-yl)methanol

HRID 472103Notes

Reaction equation

HRID 472103 reaction equation
[CH3:1][CH:2]1[CH:7]([N:8]([CH3:28])[C:9]2[C:10]3[CH:17]=[CH:16][N:15](S(C4C=CC(C)=CC=4)(=O)=O)[C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:6][CH2:5][CH:4]([CH2:29][S:30]([N:33]2[CH2:37][CH2:36][C@H:35]([CH2:38][OH:39])[CH2:34]2)(=[O:32])=[O:31])[CH2:3]1.[Li+].[OH-].CO.C1COCC1>CC(O)=O.O>[CH3:1][CH:2]1[CH:7]([N:8]([CH3:28])[C:9]2[C:10]3[CH:17]=[CH:16][NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:6][CH2:5][CH:4]([CH2:29][S:30]([N:33]2[CH2:37][CH2:36][C@H:35]([CH2:38][OH:39])[CH2:34]2)(=[O:32])=[O:31])[CH2:3]1

Participants

7

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67074420((3S)-1-((3-methyl-4-(methyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methylsulfonyl)pyrrolidin-3-yl)methanol

Product 1

HCID 67073959((3S)-1-((3-methyl-4-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methylsulfonyl)pyrrolidin-3-yl)methanol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 962WaterSolvent

Procedure

A mixture of ((3S)-1-((3-methyl-4-(methyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methylsulfonyl)pyrrolidin-3-yl)methanol (0.050 g, 0.09 mmol), LiOH (0.009 g, 0.4 mmol), MeOH (1.5 mL), THF (1.5 mL), and H2O (1.0 mL) was stirred overnight. The mixture was then treated with 1 drop AcOH and the mixture concentrated. The resulting mixture was purified using reverse phase chromatography to afford the title compound. MS for C20H31N5O3S (ESI) (MH)+ m/z=422.

Workup

  1. concentrationthe mixture concentrated
  2. customThe resulting mixture was purified

Sources & evidence

ORD record
ord-a37e4db753814ed0982dd8aabf2a41da
Source dataset
uspto-grants-2014_01
Patent number
US08633206B2

Reaction notes

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