Sodium Hydroxide → 2-(tert-butyldimethylsilyloxy)-2-(5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino) pyrimidin-2-yl)thiophen-2-yl)acetic acid

HRID 1484969Notes

Reaction equation

HRID 1484969 reaction equation
[Si:1]([O:8][CH:9]([C:15]1[S:16][C:17]([C:20]2[N:25]=[C:24]([NH:26][C:27]3[CH:31]=[C:30]([CH:32]4[CH2:34][CH2:33]4)[NH:29][N:28]=3)[C:23]([Cl:35])=[CH:22][N:21]=2)=[CH:18][CH:19]=1)[C:10]([O:12]CC)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[Si:1]([O:8][CH:9]([C:15]1[S:16][C:17]([C:20]2[N:25]=[C:24]([NH:26][C:27]3[CH:31]=[C:30]([CH:32]4[CH2:33][CH2:34]4)[NH:29][N:28]=3)[C:23]([Cl:35])=[CH:22][N:21]=2)=[CH:18][CH:19]=1)[C:10]([OH:12])=[O:11])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58169434ethyl 2-(tert-butyldimethylsilyloxy)-2-(5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophen-2-yl)acetate

Product 1

HCID 581694892-(tert-butyldimethylsilyloxy)-2-(5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino) pyrimidin-2-yl)thiophen-2-yl)acetic acidYield 63.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl 2-(tert-butyldimethylsilyloxy)-2-(5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophen-2-yl)acetate (100 mg, 0.19 mmol, 1.0 eq.) in ethanol (10 mL) was added 1 N NaOH (0.8 mL, 0.76 mmol, 4.0 eq). The mixture was stirred at room temperature for 1 hour, then, concentrated and the residue was redissolved in water. To the solution was added 1N HCl (0.8 mL) and the mixture was stirred for 0.5 h at 23° C. The solution was filtered to give 2-(tert-butyldimethylsilyloxy)-2-(5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophen-2-yl)acetic acid (60 mg, 63.3%). LC-MS (m/z): 506.0 [M+H]+.

Workup

  1. concentrationconcentrated
  2. dissolutionthe residue was redissolved in water
  3. additionTo the solution was added 1N HCl (0.8 mL)
  4. stirringthe mixture was stirred for 0.5 h at 23° C
  5. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-a76981cececd4992974cf1afa0164486
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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